TW200410634A - Synergistically acting herbicidal mixtures - Google Patents
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- TW200410634A TW200410634A TW092120131A TW92120131A TW200410634A TW 200410634 A TW200410634 A TW 200410634A TW 092120131 A TW092120131 A TW 092120131A TW 92120131 A TW92120131 A TW 92120131A TW 200410634 A TW200410634 A TW 200410634A
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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Abstract
Description
200410634 玖、發明說明: 【技術領域】 本發明係關一種協同除萎混合物。 【先前技術】 在作物保護產品中,原則上需提高活性成分之作用專一 性與可靠性,因此一種活性更加之除莠混合物是非常重要 的。 【發明内容】 本發明係有關一種協同除莠混合物,其包含協同有效量之 A)至少一種式j 3-雜環基-取代之苯甲醯基衍生物200410634 发明 Description of the invention: [Technical Field] The present invention relates to a cooperative wilt-removing mixture. [Previous technology] In crop protection products, in principle, the specificity and reliability of the action of active ingredients need to be improved, so it is very important to have a more active herbicide mixture. [Summary of the Invention] The present invention relates to a synergistic herbicide mixture comprising a synergistically effective amount of A) at least one 3-heterocyclyl-substituted benzamidine derivative of formula j
其中各代號如下列定義: R、R3為_素、CKV烷基、以碥烷基、CKV烷氧基 、、G-CV自烷氧基、Ci_Q_烷硫基、Cr(v烷亞磺醯基 或烷磺醯基; 為選自下列之雜環基··異哼唑_3_基、異呤唑_4_基 号圭$基、4,5-—氫異,口坐-3-基、4,5-二氫異号 生心基與4,5_二氫異H5-基;上述6個基團可未智 :代或經下列基團取代單次或多次:齒素、Cr〜 、 Cl Crki氧基、CrCp函烷基、CrC4-鹵烷氧基 或Ci-Cr烷硫基; 86907 200410634 R4為氫、鹵素或CrC6-烷基; R 為C1-C6-坑基, R6為氫或CrC6-燒基; 或其一種環境上可相容之鹽; 及 B)兩種選自下列各物組成之群中之除莠劑:依滅草 (imazapyr)、依滅克(imazaquin)、甲基依滅本(如犯啦她如必 methyl)、依滅莫(imazamox)、依滅比(imazapic)與依滅特 (imazethapyr); 或其一種環境上可相容之鹽; 及若需要時使用之 " ^ ^ -。職丞LOA叛化酶 抑制劑(ACC)、^基乳酸酉旨合成酶抑制劑(als)、㈣ 類、植物生長素除筹劑、植物生長素運輸抑制劑、舞 胡蘿蔔素生合成抑制劑、烯醇丙酮基莽草酸3_磷酸酉匕 合成酶抑制劑(EPSPS)、麵酿胺合成酶抑制劑、脂質^ 靖制劑、有絲***抑制劑、原。卜林原汉氧化酶抑 制劑、先合作用抑制劑、協同製劑、生長物質、細胞 壁生合成抑制劑及其他多種除莠劑。 有關一種除莠組合物’其包括除 上述疋義協同除筹混合物與至少 々 若需要時❹之至少—種界面活性劑。載劑及 此外,本發明係有關製備此 想要之植物生長之方法。 化万法’及控制不 86907 200410634 在作物保護產品中’原則上需提高活性成分之作用專— 性與可靠性。本發明之目的即在提高具除荐活性之式ί 3_雜 «取代之苯甲喊衍生物於對抗不要之有害植物上之活 性與/或選擇性。 吾:已發現,此目的可藉由本文初所定義之混合物達成 口等並發現,包含此等混合物之除莠組合物、其製法、 及控制不要之植物生長之方法。後者中則不論其成分Α)、 Β)及若需要時使用之C)之耗活性化合物是否組合或分開 凋配及訑用及其若分開施用日寺,亦不受其施用順序影響。 根據本發明混合物展現協同作用,成分八)、Β)及若需要 時使用之Q之㈣活性化合物通常應對某些作物保有相容 性。 適用為乙醯基CoA羧化酶抑制劑(ACC)之成分c為例如·· 環己烯酮肟醚類、苯氧苯氧丙酸酯類或芳基胺基丙酸類。 乙醯基乳酸酯合成酶抑制劑(ALS)特別包括咪唑啉酮類、嘧 哫基醚類、磺醯胺類或磺醯基脲類。相關之植物生長素除 _ 莠劑特別為吡啶羧酸類、2,4-D或苯唑啉(benaz〇lin)。所使用 之脂質生合成抑制劑特別指醯基替苯胺類、氯乙醯替苯胺 、硫脲類、本弗赛(benfbresate)或普弗酮(perfluid〇ne)。合適之 -有絲***抑制劑特別為胺甲酸酯類 '二硝基苯胺類、吡淀 類、布達莫(butamifos)、二甲基克達(chlorthaWimethyl (DCPA))或 抑芽素。原卟啉原IX氧化酶抑制劑實例特別指二苯基醚類 、’ 一峻類、環狀亞胺類或p比峻類。合適之光合作用抑制 劑特別指除草靈(propanil)、必汰草(pyridate)或必達伏(pyridafoi) 86907 -10- 200410634 、苯並p塞二p井酮類、二硝基苯盼類、二伸p比淀類、脉類、 夺紛類、克達松(chloridazon)、三呼類、三p井嗣類、尿喃p定類 或雙胺基甲酸酯類。協同製劑特別指環氧乙烷類。合適之 生長物質實例為芳氧烷酸類、苯甲酸類或喳啉羧酸類。”其 他多種除莠劑”咸了解係特別指活性成分二氯丙酸類、二氫 苯並呋喃類、苯基乙酸類與下文中所述未(完全)了解其作 用機轉之個別除赛劑。 其他合適之成分C為選自下列之活性化合物:醯胺類、_ 植物生長素運輸抑制劑、類胡蘿蔔素生合成抑制劑、烯醇 丙酮基莽草酸-3-磷酸酯合成酶抑制劑(EPSPS)、麩醯胺合成 酶抑制劑與細胞壁合成抑制劑。 可與式I 3-雜環基取代之苯甲醯基衍生物及根據本發明式 II化合物組合使用之除莠劑實例特別為 C1 乙醯基CoA羧化酶抑制劑(ACC),例如: -環己烯酮辟醚類,如:亞汰草(alloxydim)、克脫定 (clethodim)、克普定(cloproxydim)、賽克定(cycloxydim)、 希特定(sethoxydim)、三克定(tralkoxydim)、布特定 (butroxydim)、克弗定(clefoxydim)或特普定(tepraloxydim); -苯氧苯氧丙酸酯類,如:決丙基克丁弗(clodinafop-propargyl)(及若適當時,克昆赛(cloquintocet))、丁基賽 洛弗(cyhalofop-butyl)、甲基大克弗(diclofop-methyl)、乙 基芬諾普(fenoxaprop-ethyl)、P-乙基芬諾普、乙基芬赛普 (fenthiapropethyl)、伏寄普(fluazifop-butyl)、P-伏寄普、乙 氧乙基賀普(haloxyfop-ethoxyethyl)、甲基-賀普(haloxyfop- 86907 -11 - methyl)、P-甲基-贺普、抑殺普(isoxapyrifop)、佈克普 (propaquizafop)、乙基快殺普(quizalofop-ethyl)、P-乙基快 殺普或拜裕松(quizalofop-tefuryl);或 芳基胺基丙酸類,如:甲基-伏爛普(flamprop-methyl)或 異丙基-伏爛普; 乙醯基乳酸酯合成酶抑制劑(ALS),例如: -咪吐4 S同類,如:依滅草(imazapyr)、依滅克(imazaquin) 、甲基依滅本(imazamethabenz-methyl)(imazame)、依滅莫 (imazamox)、依滅比(imazapic)、依滅特(imazethapyr)或依 滅米特(imazamethapyr); -口密咬基醚類(pyrimidyl ethers),如:ρ比硫貝酸(pyrithiobac-acid)、p比硫貝酸 #3、雙 ρ比貝酸納(bispyribac-sodium)、 KIH-6127或皮本辛(pyribenzoxym); -續驢胺類,如:伏速爛(florasulam)、滅速爛(flumetsulam) 或特速爛(metosulam);或 -續Si基脲類,如:安速能(amidosulfUron)、阿速能 (azimsulfUron)、甲基本速能(bensulfUron-methyl)、乙基克 姆能(chlorimuron-ethyl)、克速能(chlorsulfUron)、新速能 (cinosulfUron)、賽姆能(cyclosulfamuron)、甲基乙速能 (ethametsulfuron-methyl)-乙氧速能^ (etiioxysulfUron)、伏賽 速能(flazasulfliron)、甲基賀速能(halosulfUron-methyl)、依 速能(imazosulfbron)、甲基滅速能(metsulfbron-methyl)、尼 速能(nicosulfuron)、甲基普速能(primisulfliron-methyl)、普 洛速能(prosulfUron)、乙基叶匕吐速能(pyrazosulfbron-ethyl) 200410634 、靈速能(rimsulfUron)、甲基速特能(sulfometuron-methyl) 、甲基地芬速能(thifensulfuron-methyl)、三速能 (triasulfuron)、甲基三本能(tribenuron-methyl)、甲基三伏 速能(triflusulfliron-methyl)、N-[[[4-甲氧基- 6-(三氟甲基)-1,3,5-三畊-2-基]胺基]羰基]-2-(三氟甲基)-苯磺醯胺、 石黃速能(sulfosulfuron)或碘《速能(iodosulfuron); C3 g盛胺類,例如: -艾力拉草(allidochlor)(CDAA)、乙基-苯甲酸基丙 春 (benzoylprop-ethyl)、溴汰(bromobutide)、克殺滅(chlorthiamid) 、大芬滅(diphenamid)、抑脫本(etobenzanid (benzchlomet)) 、伏赛滅(fluthiamide)、福赛明(fosamin)或莫奈得 (monalide); C4植物生長素除萘劑,例如: -口比淀叛酸類,如:陶斯松(clopyralid)或比克爛(picloram) ;或 -254»Dj^ ^ ^ # (benazolin); C5植物生長素運輸抑制劑,例如: -鋼得爛(naptalame)或大芬比(diflufenzopyr); C6類胡蘿蔔素生合成抑制劑,例如·· -本索芬(benzofenap)、克麻松(clomazone (dimethazone))、 大芬肯(diflufenican)、氟氯酮(fluorochloridone)、弗力酮 (fluridone)、口比吐靈(pyrazolynate)、p比 口坐芬(pyrazoxyfen)、 艾弗特(isoxafkitole)、艾氯特(isoxachlortole)、滅奇酮 (mesotrione)、速克酮(sulcotrione (chlormesulone))、奇特斯 86907 -13 - 200410634 (ketospiradox)、弗它蒙(flurtamone)、諾弗松(norflurazon)或 安滅特(amitrol); C7 烯醇丙酮基莽草酸-3-磷酸酯合成酶抑制劑(EPSPS),例 如: -草甘膦(glyphosate)或弗赛(sulfosate); C8 熬驢胺合成酶抑制劑,例如·· -必爛(bilanafos,bialaphos)或古弗辛铵(glufosinate-ammonium); C9脂質生合成抑制劑,例如·· 鲁 -酿基替苯胺,如:安弗斯(anilofos)或滅芬赛(mefenacet); -氯乙縫替苯胺,如··大滅驢胺(dimethenamid)、S-大滅酉蠢 胺、乙S盛拉草(acetochlor)、拉草(alachlor)、丁基拉草 (butachlor)、丁烯拉草(butenachlor)、乙基大抑草(diethathyl-ethyl)、大滅草(dimethachlor)、滅赛克(metazachlor)、滅多 草(metolachlor)、S-滅多草、普地拉草(pretilachlor)、雷蒙 得(propachlor)、普納拉草(prynachlor)、得拉草(terbuchlor) 、新拉草(thenylchlor)或赛拉草(xylachlor) ; Φ -硫脲類(thioureas),如··拔敵草(butylate)、赛克草 (cycloate)、二亞拉(diallate)、大滅普(dimepiperate)、EPTC 、依普卡(esprocarb)、稻得壯(molinate)、比布草(pebulate) 、普速卡(prosulfocarb)、殺丹(thiobencarb (benthiocarb))、 三亞拉(triallate)或萬隆(vemolate);或 -本弗賽(benfuresate)或普弗酮(perfluid〇ne); C10有絲***抑制劑,例如: -胺甲酸醋類’如··亞速爛(asulam)、卡本滅(carbetamid) 86907 -14- 200410634 、克普芬(chlorpropham)、歐本卡(orbencarb)、普拿滅 (pronamid (propyzamid))、普洛凡(propham)或狄卡巴 (tiocarbazil); -一硝基苯胺類’如:本尼芬(benefin)、比達寧(butralin) 、大芬滅(dinitramin)、乙伏靈(ethalfluralin)、弗克靈 (fluchloralin)、歐賽靈(oryzalin)、施得圃(pendimethalin)、 普得胺(prodiamine)或三福林(trifluralin); -p比淀類’如··二硫p比(dithiopyr)或p塞嗤ρ比(thiazopyr);或 布達莫(butamifos)、二甲基克達(chlorthal-dimethyl (DCPA)) 或抑芽素; C11原卟啉原IX氧化酶抑制劑,例如: -二苯基醚類,如:亞喜芬(acifluorfen)、亞喜芬鋼、亞 克芬(aclonifen)、必芬諾(bifenox)、氯硝芬(chlomitrofen) (CNP)、乙希芬(ethoxyfen)、弗地芬(fluorodien)、乙基弗 蓋芬(fluoroglycofen-ethyl)、弗賽芬(fomesafen)、弗歐芬 (fUryloxyfen)、拉克芬(lactofen)、鈉得芬(nitrofen)、硝弗 芬(nitrofluorfen)或復祿芬(oxyfluorfen); -口号二 口圭類,如:樂得奇(oxadiargyl)或 4 二松(oxadiazon); 環狀亞胺類,如:亞芬定(azafenidin)、布塔芬(butafenacil) 、乙基卡芬松(carfentrazone-ethyl)、乙基辛尼頓(cinidon-ethyl)、戊基弗克拉(flumiclorac-pentyl)、弗。咢辛(flumioxazin) 、弗普朋(flmnipropyn)、弗普希(flupropacil)、甲基弗赛 特(fluthiacet-methyl)、速芬松(sulfentrazone)或赛達明 (thidiazimin);或 86907 -15- 200410634 -吡唑類,如:ET-75卜JV 485或尼克芬(nipymclofen); C12光合作用抑制劑,例如: -除草靈(propanil)、必汰草(pyridate)或必達伏(pyridafol); -本並卩塞二卩井酮類,如:本達隆(bentazone); -一確基苯紛類,例如:撲芬辛(bromofenoxim)、大諾賽 (dinoseb)、大諾賽乙酸鹽、大諾特(din〇terb)或DNOC ; 二伸批p定類,如:賽快氯化物(cyperquat-chloride)、大 务快甲硫酸鹽(difenzoquat-methylsulfate)、大快(diquat)或 巴拉别二氯化物(paraqUat-dichloride); 月尿類’如:氯溴能(chlorbromuron)、氣特能(chlorotoluron) 、大芬速能(difenoxuron)、大滅能(dimefUron)、達有龍 (diuron)、艾滅特(ethidimuron)、芬有龍(fenuron)、弗特能 (fluometuron)、異普特能(isoproturon)、異有龍(isouron)、理 有龍(linuron)、甲苯魂有龍(methabenzthiazuron)、米它口坐 (methazole)、滅本能(metobenzuron)、滅有龍(metoxuron)、 莫理有龍(monolinuron)、尼布有龍(neburon)、西有龍 (siduron)或特理龍(tebuthiuron); -苯盼類,如:溴尼(bromoxynil)或艾歐尼(ioxynil); -克達松(chloridazon); -三p井類,如:草殺淨(ametryn)、草脫淨(atrazine)、殺淨 (cyanazine)、特敏淨(desmetryn)、地滅特(dimethamethryn)、 菲殺淨(hexazinone)、普滅頓(prometon)、普滅淨(prometryn) 、普帕淨(propazine)、草滅淨(simazine)、西米特林(simetryn) 、特佈滅(terbumeton)、特佈淨(terbutryn)、脫別淨 86907 -16- 200410634 (terbutylazine)或三汰淨(trietazine); -三_ _類,如:滅大美松(metamitron)或滅必淨(metribuzin); -尿卩密卩定類’如:克草(bromacil)、爛希(lenacil)或托拜希 (terbacil);或 -雙胺基甲酸目旨類’如:地達芬(desmedipham)或芬地凡 (phenmedipham); C13協同製劑,例如: -環氧乙虎類’如:三地芬(tridiphane); 肇 C14生長物質,例如: -芳氧fe酸類’如:2,4-DB、克普(clomeprop)、大克普 (dichlorprop)、大克普-P (2,4-DP-P)、氟氯比(fluoroxypyr)、 MCPA、MCPB、滅克普(mecoprop)、滅克普-P或三克比 (triclopyr); -苯甲酸類,如:克爛本(chloramben)或汰克草(dicamba); 或 -口奎p林叛酸類,如:快克拉(quinclorac)或快滅克(quinmerac) ; ^ C15細胞壁合成抑制劑,例如: -依賽本(isoxaben)或二氣芊腈(dichlobenil); C16其他多種除荐劑,例如: -二氯丙酸類,如:得拉本(dalapon); -二氫苯並吱喃類,如:依芬赛(ethoflxmesate); -苯基乙酸類,如:氯芬克(chlorfenac (fenac));或 -滅蘇民(aziprotryn)、巴本(barban)、本速賴(bensulide)、本 赛速能(benzthiazuron)、本弗(benzofluor)、布明弗斯 86907 -17- 200410634Each code is as follows: R, R3 are _ prime, CKV alkyl, fluorenyl, CKV alkoxy, G-CV from alkoxy, Ci_Q_ alkylthio, Cr (v alkylsulfinyl sulfonium Or an alkanesulfonyl group; a heterocyclic group selected from the group consisting of: isoxazole_3_ group, isorazol_4_yl group, 4,5--hydroiso, ortho-3- Group, 4,5-dihydroisosymbiotic group and 4,5_dihydroisoH5- group; the above 6 groups may be unwise: substituted or substituted one or more times by: Cr ~, Cl Crkioxy, CrCp-alkyl, CrC4-haloalkoxy, or Ci-Cr alkylthio; 86907 200410634 R4 is hydrogen, halogen, or CrC6-alkyl; R is C1-C6-pit, R6 Is hydrogen or CrC6-alkyl; or one of its environmentally compatible salts; and B) two herbicides selected from the group consisting of imazapyr, imazaquin ), Methyl carbamazepine (eg, if it is guilty, methyl), imazamox, imazapic, and imazethapyr; or one of its environmentally compatible salts; and Use quotation ^ ^-if needed. LOA rebel enzyme inhibitors (ACC), ^ -lactate synthase inhibitors (als), salamanders, auxins, auxin transport inhibitors, carotenoid biosynthesis inhibitors, Enolacetone shikimate 3-phosphate synthase inhibitor (EPSPS), glutamine synthetase inhibitor, lipid preparation, mitotic inhibitor, progenitor. Blint original Han oxidase inhibitors, pre-cooperative inhibitors, synergistic agents, growth substances, inhibitors of cell wall synthesis, and various other herbicides. With regard to a ridiculous composition ', it comprises a synergistic removal mixture and at least 界面, if desired, at least one surfactant. Vehicles and, moreover, the present invention relates to a method for preparing this desired plant growth. Chemical methods 'and control 86907 200410634 In crop protection products', in principle, it is necessary to improve the specificity and reliability of the active ingredients. The object of the present invention is to increase the activity and / or selectivity of the substituted benzoyl derivative with the recommended activity against undesired harmful plants. I: It has been found that this purpose can be achieved by the mixtures defined at the beginning of this article, and it has been found that the herbicidal composition containing these mixtures, its preparation method, and the method of controlling unwanted plant growth. In the latter, regardless of whether the active compounds of the components A), B) and C) used if necessary are combined or separated, they are not combined and used, and if they are applied separately, they are not affected by the order of application. According to the mixtures according to the invention, synergistic effects, the active compounds of ingredients VIII), B) and Q, if required, should generally maintain compatibility with certain crops. The component c suitable for use as an acetylcoA carboxylase inhibitor (ACC) is, for example, a cyclohexenone oxime ether, a phenoxyphenoxypropionate, or an arylaminopropionic acid. Acetyl lactate synthase inhibitors (ALS) include, in particular, imidazolinones, pyrimidinyl ethers, sulfonamides or sulfonylureas. Related auxin tinctures are, in particular, pyridinecarboxylic acids, 2,4-D or benazolin. The lipid biosynthesis inhibitors used specifically refer to fluorenilidine, chlorhexidine, thiourea, benfbresate or perfluidone. Suitable-Mitotic inhibitors are in particular carbamates' dinitroanilines, pyridines, butamifos, chlorthaWimethyl (DCPA) or statin. Examples of protoporphyrinogen IX oxidase inhibitors specifically refer to diphenyl ethers, monoamines, cyclic imines, or p-isocyanates. Suitable photosynthesis inhibitors are in particular propanil, pyridate or pyridafoi 86907 -10- 200410634, benzo-p-diphenyl-p-ketones, dinitrophenpans, di Extender p-type, vein-type, destructive-type, chloridazon, tri-type, tri-type wells, urethane-type or bis-carbamate. Synergistic formulations specifically refer to ethylene oxides. Examples of suitable growth substances are aryloxyalkanoic acids, benzoic acids or xanthroline carboxylic acids. The term "other various herbicides" refers specifically to the active ingredients dichloropropionic acid, dihydrobenzofuran, phenylacetic acid, and individual herbicides whose functional mechanism is not fully understood as described below. Other suitable ingredient C is an active compound selected from the group consisting of amidines, auxin transport inhibitors, carotenoid biosynthesis inhibitors, enolacetone shikimate-3-phosphate synthase inhibitors (EPSPS ), A glutamine synthetase inhibitor and a cell wall synthesis inhibitor. Examples of herbicides that can be used in combination with 3-heterocyclyl-substituted benzamidine derivatives and compounds of formula II according to the invention are, in particular, C1 ethylammonium CoA carboxylase inhibitors (ACC), such as:- Cyclohexenone ethers, such as: alloxydim, clethodim, cloproxydim, cycloxydim, sethoxydim, and tralkoxydim , Butroxydim, clefoxydim or tepraloxydim; -phenoxyphenoxypropionates, such as: clodinafop-propargyl (and if appropriate, Cloquintocet), cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, P-ethylfenopre, B Fenthiapropethyl, fluazifop-butyl, P-voxip, haloxyfop-ethoxyethyl, haloxyfop- 86907 -11-methyl, P-methyl-hop, isoxapyrifop, propaquizafop, quizalofop-ethyl, P-ethyl Or quizalofop-tefuryl; or arylaminopropionic acids, such as: flamprop-methyl or isopropyl-vofuran; acetamyl lactate synthase inhibition (ALS), for example:-Mito 4 S, like: imazapyr, imazaquin, imazamethabenz-methyl (imazame), imazamox , Imazapic, imazethapyr, or imazamethapyr; -pyrimidyl ethers, such as: pirithiobac-acid, p ratio Thiobetic acid # 3, bispyribac-sodium, KIH-6127 or piribenzoxym; -continuous donkey amines, such as: florasulam, flumetsulam Or metosulam; or -continuous Si-based ureas, such as: amidosulfUron, azimsulfUron, bensulfUron-methyl, chlorimuron- ethyl), chlorsulfUron, cinosulfUron, cyclosulfamuron, ethametsulfuron-methyl- EtiioxysulfUron, flazasulfliron, halosulfUron-methyl, imazosulfbron, metsulfbron-methyl, nicosulfuron ), Primisulfliron-methyl, prosulfUron, pyrazosulfbron-ethyl 200410634, rimsulfUron, sulfometuron- methyl), thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triflusulfliron-methyl, N-[[[4- 甲Oxy-6- (trifluoromethyl) -1,3,5-trigen-2-yl] amino] carbonyl] -2- (trifluoromethyl) -benzenesulfonamide sulfosulfuron) or iodine (iodosulfuron); C3 g amines, for example:-Allidochlor (CDAA), ethyl-benzoate-propionate (benzoylprop-ethyl), bromobutide , Chlorthiamid, diphenamid, etobenzanid (benzchlomet), fluthiamide, blessing Fosamin or monalide; C4 auxin denaphthalenes, for example:-Kopital acid, such as: clopyralid or picloram; or -254 »Dj ^ ^ ^ # (benazolin); C5 auxin transport inhibitors, for example:-steel naptalame or diflufenzopyr; C6 carotenoid biosynthesis inhibitors, for example ...-benzofenap , Clomazone (dimethazone), diflufenican, fluorochloridone, fluridone, pyrazolynate, pyrazoxyfen, ai Isoxafkitole, isoxachlortole, mesotrione, sulcotrione (chlormesulone), 86907 -13-200410634 (ketospiradox), flurtamone, norfo Norflurazon or amitrol; C7 enolacetone shikimate-3-phosphate synthase inhibitor (EPSPS), for example: -glyphosate or sulfosate; C8 Donkey amine synthetase inhibitors, such as--will rot (bilanafos bialaphos) or glufosinate-ammonium; C9 lipid biosynthesis inhibitors, such as Lu-glycine, such as: anilofos or mefenacet;-chloroethene Tfeniamine, such as dimethenamid, S-dimethenamid, acetochlor, alachlor, butachlor, butenes ( butenachlor, diethathyl-ethyl, dimethachlor, metazachlor, metolachlor, S-phenanthrene, pretilachlor, raymond (Propachlor), prynachlor, terbuchlor, thenylchlor or xylachlor; Φ-thioureas, such as butylate ), Cycloate, diallate, dimepiperate, EPTC, esprocarb, molinate, pebulate, prosulfocarb ), Thiobencarb (benthiocarb), triallate or vemolate; or-benfuresate or general PerfluidOne; C10 mitotic inhibitors, for example:-carbamates such as asulam, carbetamid 86907 -14- 200410634, chlorpropham, Orbencarb, pronamid (propyzamid), propham or tiocarbazil;-Mononitroanilines' such as: benefin, bidanin ( butralin, dinitramin, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine or trifluralin; -p ratio lakes, such as dithiopyr or thiazopyr; or butamifos, chlorthal-dimethyl (DCPA), or bud suppression C11 protoporphyrinogen IX oxidase inhibitors, for example:-diphenyl ethers, such as: acifluorfen, axifen steel, aclofen, bifenox, Chlomitrofen (CNP), ethoxyfen, fluorodien, fluoroglycofen-eth yl), fomesafen, fUryloxyfen, lactofen, nitrofen, nitrofluorfen or oxyfluorfen;-slogans of two guinea pigs , Such as: oxadiargyl or oxadiazon; cyclic imines, such as: azafenidin, butafenacil, carfentrazone-ethyl, ethyl Cicinon-ethyl, flumiclorac-pentyl, ethno. Flumioxazin, flmnipropyn, flupropacil, fluthiacet-methyl, sulfurtrazone or thidiazimin; or 86907 -15- 200410634 -Pyrazoles, such as: ET-75, JV 485 or nipymclofen; C12 photosynthesis inhibitors, such as:-propanil, pyridate, or pyridafol;-the present Dioxin ketones, such as: Bentazone;-A benzene group, such as: bromofenoxim, dinoseb, danosyl acetate, dano Dinoterb or DNOC; two types of p-types, such as: Cyperquat-chloride, difenzoquat-methylsulfate, diquat, or Parabet Chloride (paraqUat-dichloride); Lunauria such as: chlorbromuron, chlorotoluron, difenoxuron, diefoxon, diuron, diuron, Ethidimuron, fenuron, fluometuron, isoprotu ron), isouron, linuron, methabenzthiazuron, methazole, metobenzuron, metoxuron, morrison (Monolinuron), neburon, siduron, or tebuthiuron;-phenpanes, such as: bromoxynil or ioxynil;-kedarson (Chloridazon); -Three p wells, such as: ametryn, atrazine, cyanazine, desmetryn, dimethamethryn, phenanthrene ( hexazinone), prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbume ( terbutryn), 86907 -16- 200410634 (terbutylazine) or tritazine;-three _ _ types, such as: metamitron or metribuzin;-urine tightness Classes such as: bromacil, lenacil, or terbacil; or-bisamino acid orders such as: desmedipham or Phenmedipham; C13 synergistic preparations, for example: -Ethoxylates such as: tridiphane; C14 growth substances, for example: -aryloxyfe acids, such as: 2,4-DB, Clomeprop, dichlorprop, dikeprop-P (2,4-DP-P), fluoroxypyr, MCPA, MCPB, mecoprop, mecoprop- P or triclopyr;-benzoic acids, such as: chloramben or dicamba; or-quinacorac acid, such as: quinclorac or quinclorac (Quinmerac); ^ C15 cell wall synthesis inhibitors, such as:-Isoxaben or dichlobenil; C16 other various recommenders, such as:-Dichloropropionic acids, such as: delaben ( dalapon);-dihydrobenzos, such as: ethoflxmesate;-phenylacetic acids, such as: chlorfenac (chlorac) (fenac); or-aziprotryn, Baben (Barban), Bensulide, Benzthiazuron, benzofluor, Bloomings 86907 -17- 200410634
(buminafos)、布達吐(buthidazole)、布特龍(buturon)、卡芬特 (cafenstrole)、克布芬(chlorbufam)、甲基克芬普(chlorfenprop-methyl)、氯速能(chloroxuron)、辛滅靈(cinmethylin)、庫有 龍(cumyluron)、賽有龍(cycluron)、賽布畊(Cyprazine)、賽 口坐(cyprazole)、二苄有龍(dibenzyluron)、二普特靈 (dipropetryn)、達姆龍(dymron)、乙基艾格淨(eglinazin-ethyl) 、安塔(endothall)、依特辛(ethiozin)、弗卡松(flucabazone) 、弗本塔尼(fluorbentranil)、弗普散(flupoxam)、艾卡滅 (isocarbamid)、艾普靈(isopropalin)、卡布滅(karbutilate)、滅 弗地(mefluidide)、蒙有龍(monuron)、納普滅(napropamide) 、納普列(napropanilide)、納赛靈(nitralin)、歐希克芬 (oxaciclomefone)、芬艾凡(phenisopham)、比弗斯(piperophos) 、普赛畊(procyazine)、普弗靈(profluralin)、普地卡 (pyributicarb)、希肯頓(secbumeton)、硫亞拉(sulfallate (CDEC)) 、特布卡(terbucarb)、三亞凡(triaziflam)、***芬滅 (triazofenamid)或三米特能(trimeturon); 或其環境上相容之鹽。 式I 3-雜環基取代之苯甲醯基衍生物揭示於WO 96/26206、 WO 97/41116、WO 97/41117 與 WO 97/41118、W〇 98/31681。 來自B與C1至C16族群中之除莠劑活性化合物說明於例 如: - ’’Herbizide[除葬劑]’’,Hock,Fedtke,Schmidt,第一版, Thieme 出版 ’ 1995(參見’,快克拉(quinclorac)’’ ρ· 238,’’稻得 壯(molinat)’’ ρ· 32,’’ 丁 基拉草(butachlor)’’ ρ· 32,π 普地拉草 86907 -18- 200410634(buminafos), buthidazole, buturon, cafenstrole, chlorbufam, chlorfenprop-methyl, chloroxuron, Cinmethylin, cumyluron, cycluron, cyprazine, cyprazole, dibenzyluron, dipropetryn , Dymron, eglinazin-ethyl, endothall, ethiozin, flucabazone, fluorbentranil, fupusan ( flupoxam, isocarbamid, isopropalin, karbutilate, mefluidide, monuron, napropamide, napropanilide ), Nitralin, oxaciclomefone, phenisopham, piperophos, procyazine, profluralin, piributicarb ), Secbumeton, sulfallate (CDEC), terbucar b), triaziflam, triazofenamid or trimeturon; or an environmentally compatible salt thereof. 3-Heterocyclyl-substituted benzamidine derivatives of formula I are disclosed in WO 96/26206, WO 97/41116, WO 97/41117 and WO 97/41118, WO 98/31681. Herbicide active compounds from the B and C1 to C16 groups are described, for example:-"Herbizide [Fericide]", Hock, Fedtke, Schmidt, 1st edition, published by Thieme '1995 (see' Quick Carat (Quinclorac) ρ · 238, `` molinat '' ρ · 32, `` butachlor '' ρ · 32, π pudira grass 86907 -18- 200410634
(pretilachlor)’’ ρ· 32,’’ 二硫 p比(dithiopyr)’1 ρ· 32,’’ 滅芬赛 (mefenacet)’’ ρ· 32,π 乙基芬諾普(fenoxapropethyl),,ρ· 216,,,大 滅普(dimepiperate)’’p. 32,’’ρ比 口圭靈(pyrazolynate)” ρ· 146,π 口比 峻芬(pyrazoxyfen)np· 146,’’ 甲基本速能(bensulfUron-methyl)" ρ· 31,11 乙基 p比口坐速能(pyrazosulfUron-ethyl) ’’ ρ· 31,’’ 新速能 (cinosulfUron)’’ ρ· 31,’,本弗赛(benfbresate)’’ ρ· 233、π 溴汰 (bromobutide)’’ ρ· 243,’’達姆龍(dymron)1’ ρ· 243,’’二甲基草 殺淨(dimethyametryn)π ρ· 118,π 依普卡(esprocarb) ” ρ· 229,’’ 普 地卡(pyributicarb)’· ρ· 32,” 希滅靈(cinemthylin)’’ ρ· 32,π 除草 靈(propanil)’’ ρ· 32,’’2,4-D” ρ· 30,,’ 本達隆(bentazon),’ ρ· 30,(pretilachlor) ρ 32, `` dithiopyr '1 ρ 32, `` mefenacet' 'ρ 32, π fenoxapropethyl, ρ · 216 ,,, dimepiperate `` p. 32, "ρ pyrazolynate ρ 146, π pyrazoxyfen np 146, '' methyl local speed (BensulfUron-methyl) " ρ · 31,11 Ethyl p specific sitting speed energy (pyrazosulfUron-ethyl) '' ρ 31, `` CinosulfUron '' ρ 31, ', Ben Fusai (Benfbresate) ρ · 233, π bromobutide ρ 243, `` dymron 1 'ρ 243,' 'dimethyametryn π ρ · 118 , Π esprocarb ”ρ · 229,” piributicarb '· ρ · 32, “cinethylin” ρ · 32, π propanil ”ρ · 32, "2,4-D" ρ · 30 ,, 'Bentazon,' ρ · 30,
’’阿速能(azimsulfUron)(DPX-A-8947)’’ ρ· 175,’’ 滅克普-P (mecoprop-P)’’ ρ· 237,’’克普芬(chlorpropham)’’ ρ· 205,n 乙希 芬(ethoxyfen)’’ ρ_ 30,’’ 甲基贺普(haloxyfop-P-methyl’1 ρ· 38, π乙氧乙基賀普(haloxyfop-ethoxyethyl)n ρ· 38,π戊基伏克拉 (flumiclorac-pentyl)·1 ρ· 35,·’弗普希(flupropacil)’’ ρ· 143,π尼克 芬(nipyraclofen)” ρ· 145,π 特速爛(metosulam)'’ ρ· 33,’’ 甲基乙 速能(ethametsulfUron-methyl)’’ ρ· 36,π 甲基地芬速能 (thifensulfliron-methyl)’’ ρ· 35,’’叶匕硫貝酸(pyrithiobac acid),,ρ· 181); "Agricultural Chemicals’’,第 II冊除莠劑,1993(參見 π殺丹 (thiobencarb)’· ρ· 85,π 本吐芬(benzofenap)’’ ρ· 221,’’納普列 (napropanilid)’’ ρ· 49,π 比弗斯(piperophos)’’ ρ· 102,’’安弗斯 (anilofos)’’ ρ· 241,’’依速能(imazosulfUron)(TH-913)n ρ· 150, ”依本滅(etobenzamid)(HW-52)’’ ρ· 54,丨’速克嗣(sulcotrione) 86907 -19- 200410634 (ICIA-0051)’’ p. 268,’’普賽(poast)’’ ρ· 253,’,伏克斯(focus)’’ ρ· 222,’’ 大滅醯胺(dimethenamid)1’ ρ· 48,n 弗賽(sulfosate)1’ ρ· 236,’’2,4-DB” ρ· 10,’’大克普-P (dichlorprop-P)’’ ρ· 6,’’ 弗普 散(flupoxam)" ρ· 44,π 普速卡(prosulfocarb)ff ρ. 84,’’ 快滅克 (quinmerac)’f ρ· 233,π 滅赛克(metazachlor)’丨 ρ· 64,"弗它蒙 (flurtamone)π ρ· 265,π 撲芬辛(bromofenoxim)π ρ. 228,π 弗賽芬 (fomesafen)π ρ· 248,’’ 甲基依滅本(imazamethabenz-methyl)π ρ· 153,π块丙基克丁弗(clodinafop-propargyl)’’ ρ· 214,’’Ρ-乙基 芬諾普(fenoxaprop-P-ethyl)n ρ. 208,’’Ρ-丁基伏寄普(£11^也(^-P-butyl)n ρ· 207,’’Ρ-乙基快殺普(quizalofop-P-ethyl)" ρ. 210, ’’拜裕松(quizalofop-terfUryl)’’ ρ· 211,’’弗崎辛(flumioxaxin)’’ ρ· 43,n普弗朋(flumipropyn)ffp· 267,n速芬松(311脱11加2〇116)|’卩· 261,%塞口坐口比(thiazopyr)’’p. 226,比硫貝酸鈉(卩}^1:1^〇5&〇 sodium)’’ ρ· 266,’’ 滅速爛(flumetsulam)’’ ρ· 227,’’ 安速能 (&!111<1〇3111^111〇11)”卩.151,”甲基賀速能(11&1〇31111[111'〇11-11^1:]1}4)’|口· 148,’’ 靈速能(rimsulfUron)” ρ· 138,’’ 甲基三本能(1:1化€11111:〇11-methyl)’’ ρ·139,’’ 甲基地芬速能(triflusulfbron-methyl)’’ ρ· 137, ’’普速能(primisulfUron-methyl)’1 ρ· 147); ’’Agricultural Chemicals1’,第 II冊除莠劑,第 13 版(參見’’卡 芬特(carfenatole)” ρ· 284,丨’績速能(sulfosulfUron)’’ ρ· 145,’’ 乙 氧速能(ethoxy-sulfbron)’’ ρ· 149,’’ 皮本辛(pyribenzoxym)’’ ρ· 279 ,’’二芬比(diflufenzopyr)’,ρ· 90,’ΈΤ-75Γ ρ· 278,’,乙基卡芬 松(carfentrazone-ethyl) ’’ ρ· 267,’’ 甲基弗赛特(fluthiacet-methyl) ’’ ρ· 277,’’依滅比(imazapic)i’ ρ· 160,’’ 谢希拉草(butenachlor)’’ 86907 -20- 200410634 ρ· 54,’’狄卡巴(tiocarbazil)1’ ρ· 84,π 伏赛滅(fluthiamide)1’ ρ· 62 ,’’艾弗特(isoxaflutole)” ρ· 283,’’布特定(butroxydim)n ρ· 259);'' AzimsulfUron (DPX-A-8947) '' ρ 175, `` Mecoprop-P '' ρ 237, `` chlorpropham '' ρ · 205 , n ethoxyfen "ρ_ 30 ," haloxyfop-P-methyl'1 ρ · 38 , π ethoxyfen-ethoxyethyl n ρ · 38 , πflumiclorac-pentyl · 1 ρ · 35 , '' flupropacil 'ρ · 143, πnicraclofen' ρ · 145, π metosulam '' ρ · 33 , "ethametsulfUron-methyl" ρ · 36 , π thifensulfliron-methyl "ρ · 35 ," pyrithiobac acid (, Ρ 181); " Agricultural Chemicals '', Book II Herbicides, 1993 (see thiobencarb '· ρ 85, π benzofenap' 'ρ 221,' 'Napropanilid' ρ 49, π piperophos ρ 102, `` anilofos '' ρ 241, `` imazosulfUron '' ( TH-913) n ρ · 150, "etobenzamid (HW-52)" ρ · 54, 丨 'sulcotrione 86907 -19- 200410634 (ICIA-0051)' 'p. 268 "Poast" ρ 253, ', Focus' ρ 222,' 'Dimethenamid 1' ρ 48, n sulfosate 1 'ρ · 236, `` 2,4-DB "ρ · 10,` `Big Kep-P (dichlorprop-P)' 'ρ · 6,` `fluxam " ρ · 44, π Prosulfocarb ff ρ. 84, '' quinmerac'f ρ · 233, π metazachlor '丨 ρ 64, " flurtamone π ρ · 265 , Π bromofenoxim π ρ. 228, π fomesafen π ρ · 248, '' imazamethabenz-methyl π ρ 153, π block propyl kefir ( clodinafop-propargyl) '' p. 214, '' fenoxaprop-P-ethyl) n p. 208, `` p-butyl voltopor (£ 11 ^ 也 (^ -P- butyl) n ρ · 207, "quizalofop-P-ethyl" " ρ. 210, '' by Pine (quizalofop-terfUryl) "ρ · 211," Fluzoxaxin "ρ · 43, n Flumipropyn (ffp · 267), n-speed Fenson (311 off 11 plus 2016) | '卩 · 261,% plug mouth sitting ratio (thiazopyr) `` p. 226, sodium thiobepyrate (卩) ^ 1: 1 ^ 〇5 & 〇sodium) ρ · 266,' ' Rotten (flumetsulam) ρ · 227, "A & S (&! 111 < 1033111 ^ 111〇11)", " 151. " 11-11 ^ 1:] 1} 4) '| mouth · 148, "rimsulfUron" ρ, 138, "methyl tristint (1:11 € 11111: 〇11-methyl)' 'ρ · 139, `` triflusulfbron-methyl' 'ρ · 137, `` primisulfUron-methyl'1 ρ · 147);' 'Agricultural Chemicals1', Book II except Tincture, 13th Edition (see "carfenatole" ρ · 284, 丨 'sulfosulfUron' ρ · 145, `` ethoxy-sulfbron '' ρ · 149, "pyribenzoxym" ρ · 279, "two Ratio (diflufenzopyr), ρ · 90, 'ΈΤ-75Γ ρ · 278,', carfentrazone-ethyl '' ρ · 267, `` fluthiacet-methyl '' ρ · 277, `` imazapic i 'ρ · 160,' 'butenachlor 86907 -20- 200410634 ρ 54, `` tiocarbazil 1' ρ 84, π fluthiamide 1 'ρ · 62, "isoxaflutole" ρ 283, "butroxydim n ρ · 259);
Short Review of Herbicides & PGRs 1991,Hodogaya Chemicals (參 見 n 弗歐芬(fbryloxyfen)1’ ρ· 142,”三峻芬滅(triazofenamid)'’ ρ· 268,'塞吩氯(thenylchlorid)(NSK-850)’’ ρ· 52,π 庫有龍 (cumyluron)(JC-940)” ρ· 90,’’施得圃(pendimethalin)(AC_92553)’’ ρ· 58,’’布達吐(buthidazole)’’ ρ· 88,’’赛口坐(cyprazole)1’ p. 38,Short Review of Herbicides & PGRs 1991, Hodogaya Chemicals (see n fbryloxyfen 1 'ρ 142, "triazofenamid" ρ 268,' thenylchlorid (NSK- 850) "ρ 52, π cumyluron (JC-940)" ρ 90, "pendimethalin (AC_92553)" ρ 58, "buthiazole" ρ 88, '' cyprazole 1 'p. 38,
’’艾力拉草(allidochlor)n ρ· 48,’’乙基-苯甲醯基丙〇^112(^一叩-ethyl)’’ ρ· 38,’’ 克殺滅(chlorthiamid)1’ ρ· 150,’’ 大芬滅 (diphenamid)’’ ρ· 34,π 甲基-伏爛普(flamprop_methyl)’’ ρ· 40, π 福賽明(fosamin)π ρ· 232,’’依賽本(isoxaben)π ρ· 42,π 莫奈得 (monalide)” ρ· 32,11 納得爛(naptalam)n ρ· 36,n 普拿滅 (pronamid)’’ ρ· 34,’’ 必爛(bialaphos)’’ ρ· 234,’’ 古弗辛铵 (glufosinate-ammonium)n ρ· 234,π 草甘膦(glyphosate)’’ ρ. 232, π 安滅特(amitrol)’’ ρ. 254,Μ 克普(clomeprop)’’ ρ· 20,’’ 大克普 (dichlorprop)’’ ρ_ 6,’丨芬普(fenoprop)’’ ρ. 8,π 氟氯比(fluroxypyr)’’ ρ· 156,’fMCPAn ρ· 4,nMCPB” ρ· 8,π 滅克普(mecoprop)” ρ· 6 ,”納普滅(napropamide)n ρ· 16,’’三克比(tridopyr)’’ ρ· 154, n 克爛本(chloramben)’’ ρ· 28,n 汰克草(dicamba)’’ ρ· 26,n 克麻 松(clomazone)’’ ρ. 268,’’ 大芬肯(diflufenican)’’ ρ. 42,π 氟氯酮 (fluorochloridone)’’ ρ· 266,π 弗力酮(fluridone)’’ ρ· 156,’’亞速爛 (asulam)1’ ρ· 12,’’ 巴本(barban)’’ ρ_ 100,’’拔敵草(butylate)’’ ρ_ 106 ,”卡特酸胺(carbetamide)1’ ρ· 6,n 克布凡(chlorobufam)’’ ρ· 100 ,’’赛克草(cycloate)’· ρ· 108,’’ 地達芬(desmedipham)’’ ρ· 104, 86907 -21 - 200410634 π 二亞拉(di-allate)’’ ρ· 106 ’ "EPTC" ρ· 108,’’歐本卡(orbencarb)’’ p. 112,’’ 比布草(pebulate)’’ ρ· 106,’’芬艾凡(phenisopham)’’ ρ· 118,π 芬地凡(phenmedipham)’’ ρ· 104,,f 普洛凡(propham)’,ρ. 100,’’硫亞拉(sulfallate)’’ ρ· 110,丨丨特布卡(terbucarb),’ ρ· 102, ’’三亞拉(tri-allate)’’ ρ· 108,’’ 萬隆(vemolate),,ρ· 108,’,乙醯拉 草(acetochlor)1’ ρ· 48,’’拉草(alachlor)’,ρ· 46,,’ 乙基大抑草 (diethathyl-ethyl)’’ ρ· 48,’’大滅草(dimethachlor),,ρ· 50,,,滅多 草(metolachlor)’’ ρ· 46,’’ 雷蒙得(propachbr),’ ρ· 44,,,普鈉拉 草(prynachlor)·’ ρ· 44,π 得拉草(terbuchlor)’,ρ· 48,,,赛拉草 (xylachlor)’’ ρ· 52,” 亞汰草(alloxydim),’ ρ· 260,,,克脫定 (clethodim)’’ ρ· 270,’’克普定(d〇proXydim),,ρ· 268,’,三克定 (tralkoxydim)1’ ρ· 270,’’得拉本(dalapon),,ρ· 212,,,依芬赛 (ethofhmesate)” ρ· 124,π 本尼芬(benefin),,ρ· 54,,,比達寧(butralin),, ρ· 58 ’ ’’ 大务滅(dinitramin)’’ ρ· 56,’’ 乙伏靈(ethalfluralin)’’ ρ· 60 ,’’弗克靈(fluchloralin)’’ ρ. 54,,,艾普靈(iS0pr0palin),,ρ· 58, "納赛靈(nitralin)’’ ρ· 58,’’歐賽靈(oryzalin)” ρ· 60,,,普得胺 (prodiamine)’’ ρ· 62,’’普弗靈(profluralin)” ρ· 54,π 三福林 (trifluralin)’’ ρ_ 54,’’ 大諾赛(dinoseb),,ρ· 128,,,大諾賽乙酸鹽" ρ· 128,’’大諾特(dinoterb)” ρ· 128,,,DNOCn ρ· 126,,,亞喜芬 鈉(acifluorfen-sodium),’ ρ· 142,’,亞克芬(adonifen)” ρ· 146,” 必 务諾(bifenox)’’ ρ· 140 ’ π 氯硝芬(chlomitrofen)1’ ρ· 138,’’ 大芬 速能(difenoxuron)’’ ρ· 76,’’ 弗地芬(fluor〇difen),,ρ· 138,,,乙基 弗蓋芬饵11〇1*(^如(^11々1^1),’?.146,,’拉克芬(1&〇1(^11),,口.144 ,’’鈉得芬(nitrofen)’’ ρ· 136,,,硝弗芬(nitrofluorfen)” ρ· 14〇, 86907 -22- 200410634 ’’復祿芬(oxyfluorfen)’’ ρ· l4〇,,’ 賽快氯化物(cyperquat-chloride)’’ ρ· 158,π 大芬快甲硫酸鹽(difenzoquat-methylsulfate)" ρ· 160,’’ 大快(diquat)” ρ· 158,·’ 巴拉刈二氯化物(paraquat-dichloride)11 ρ· 158,π 甲苯卩塞有龍(benzthiazuron)’’ p. 82,’’布特龍(buturon)’’ ρ· 66,’’ 氯溴能(chlorbromuron)” ρ· 72,’’ 氯速能(chloroxuron)’’ ρ· 76,n 氯特能(chlorotoluron)” ρ· 74,n 賽有龍(cycluron)·’ ρ· 84 ,n 大滅能(dimeforon)’’ ρ· 88,f’達有龍(diuron)n ρ· 70,n 艾滅 特(ethidimuron)n ρ· 86,π 芬有龍(fenuron)’· ρ· 64,π 弗特能 (fluometuron)’’ ρ· 68,ff 異普特能(isoproturon)” ρ· 80,π 異有龍 (isouron)’’ ρ· 88,π 卡布滅(karbutilate)’’ ρ· 76,’’ 理有龍(linuron)" p. 72,π 甲苯 p塞有龍(methabenzthiazuron)’’ ρ· 82,’’ 滅有龍 (metoxuron)’’ ρ· 72,’’莫理有龍(monolinuron)’’ ρ· 66,π 蒙有龍 (monuron)” ρ· 64,π 尼布有龍(neburon)·1 ρ· 72,’丨西有龍 (siduron)’1 ρ· 68,ff 特理龍(tebuthiuron)” ρ· 86,’’三米特能 (trimeturon)’’ ρ· 64,” 艾卡滅(isocarbamid)” ρ· 168,ff 依滅米特 (imazamethapyr)” p_ 172,’’依滅草(imazapyr)” ρ· 170,’’依滅克 (imazaquin)丨’ ρ· 170,’’依滅特(imazethapyr)’’ ρ· 172,’’methazole” ρ· 162,fft?号二松(oxadiazon)’’ ρ· 162,’’三地芬(tridiphane)丨f p. 266,’’溴尼(bromoxynil)ff ρ· 148,’’艾歐尼(ioxynil)’’ ρ· 148, π甲基大克弗(diclofop-methyl)” ρ· 16,π乙基芬賽普 (fenthiapropethyl)’’ ρ· 20,’’優寄普(fluazifop-butyl)’’ ρ. 18,’’ 甲 基-賀普(haloxyfop-methyl)n ρ·18,π抑殺普(isoxapyrifop)’’ ρ. 22 ,’’佈克普(propaquizafop)’’ ρ· 24,π 乙基快殺普@1^&1〇£〇卩-ethyl)’’ ρ· 20,π 氯芬克(chlorfenac)’’ ρ· 258,π 甲基克芬普 86907 -23 - 200410634 (chlorfenprop-methyl)’’ ρ· 258,"克達松(chl〇ridazon)’’ ρ· 174, π 抑芽素(maleic hydrazide)’f ρ· 162,丨,諾伏松(norflurazon)’’ ρ. 174 ,’’必汰草(pyridate)’1 ρ· 176,,,陶斯松(clopyralid),’ ρ· 154, ’’比克爛(picloram)" ρ· 154,π 乙基克姆能(chlorimuron-ethyl)’’ ρ· 92,π 克速能(chlorsulfUron)π ρ· 92,’’ 伏賽速能(flazasulfliron)π ρ· 96,” 甲基滅速能(metsulfliron-methyl)’’ ρ. 92,’’ 尼速能 (11比0311他]:011)’’卩.96,”甲基速特能(3111^011161:111'011-111€1:11;/1)’’口.92 ,’’三速能(triasulfUron)’’ ρ. 94,,,草殺淨(ametryn),,ρ· 198, π 草脫淨(atrazine)n ρ· 188,π 艾普淨(aziprotryne)” ρ· 206,”殺 淨(cyanazine)’f ρ· 192,π 賽布畊(Cyprazine)" ρ· 192,π 地滅淨 (desmetryne)” ρ· 200,π 二普特靈(dipropetryn)’’ ρ· 202,’’ 乙基艾 格淨卜81丨1^丨11<&>4)”卩.208,”菲殺淨(1^\32丨11〇1^)”9.208, π 普賽畊(procyazine)” ρ. 192,π 普滅頓(prometone)” ρ· 196, π普滅淨(pr〇metryn)n ρ· 196,π普帕淨(propazine)1’ ρ· 188,’’希 肯頓(secbumeton)n ρ. 196,π 草滅淨(simazine)’’ ρ· 188,π 西米 特林(simetryn)n ρ· 196,” 特佈滅(terbumeton)’’ ρ· 204,π 特佈 淨(terbutryn)1’ ρ· 198,π 脫別淨(terbutylazine)11 ρ· 190,π 三汰淨 (trietazine)’’ ρ· 188,’’抑脫淨(ethiozine)’’ ρ· 210,’’ 滅大美松 (metamitron)’’ ρ· 206,’’ 滅必淨(metribuzin)’’ ρ· 202,’’ 克草 (bromacil)’’ ρ· 180,’f 爛希(lenacil)’1 ρ· 180,’’托拜希(terbacil)1’ ρ. 180,’’ 苯吐琳(benazolin)’’ ρ· 262,’’ 本速賴(bensulide)’’ ρ· 228, ’’本弗(benzofluor)’’ ρ· 266,’’布達莫(butamifos)’’ ρ. 228, ,,DCPA” ρ· 28,,’ 二氯苄腈(dichlobenil)’’ ρ· 148,’,安塔 (endothal)” ρ· 264,’’滅弗地(mefluidide)’’ ρ· 306,’’普弗酮 86907 -24- 200410634 (perfluidone)’’ ρ· 260,’’得拉草(terbuchlor)’’ ρ· 48); - "Global Herbicide Directory” 第一版,1994(參見’’樂得奇 (oxadiargyl)’’ ρ· 96); - "European Directory of Agrochemical Products" Vol.2 - Herbicidesf, ,第四版(參見f’布明弗斯(buminafos)11 p. 255)。 - ’’The Pesticide Manual,第 12版,2000(參見’’雙 p比貝酸鈉 (bispyribac-sodium)’’ p. 97,伏速爛(florasulam) ρ· 420,’’賽姆 能(cyclosulfamuron)’’ ρ· 217,’’普地拉草(pretilachlor)’’ ρ· 755)。 此外,化合物”DEH-ld^示於歐洲專利申請案ΕΡ-Α 302 203 中。化合物”特普定(tepraloxydim)”說明於DE-A 33 36 140中;化 合物”乙基辛尼頓(cinidon-ethyl)’’說明於DE-A 36 03 789中。化合 物π弗本塔尼(fluorbentranil)π說明於EP-A 84 893中。其他化合物 係自’’ 1993年布萊頓作物保護會議-雜草(Brighton Crop Protection Conference-Weeds-1993)’f 中已知(參見’’賽達明(thidiazimin)’’ p_ 29, ,’AC-322140” ρ· 41,,’KIH-6127,’ ρ· 47,” 普洛速能(prosulflnOn)’,ρ· 53, ΠΚΙΗ-2023Π ρ· 61,’’滅本能(metobenzuron)" ρ· 67)。化合物 π(卡芬 妥(carfenstmle)(CH-900)n說明於 ΕΡ-Α 332 133 中,化合物Ν-[[[4-甲氧基-6-(三氟甲基)-1,3,5-三畊-2-基]胺基]-羰基]-2-(三氟甲 基苯磺醯胺)說明於PCT/EP 96/03996。 各作用機轉所指定之活性成分係基於目前之知識。若一 種活性成分適用於多種機轉時,此物質僅指定於一種作用 模式。 式I 3-雜環基-取代之苯甲醯基衍生物可呈純對映異構物 使用,亦可呈消旋物或非對映異構性混合物使用。 86907 25 - 200410634 式I 3-雜環基-取代之苯甲醯基衍生物與/或來自b族群中 之除莠活性化合物與/或來自C1SCi6族群中之除莠活性化 合物亦可呈其一種環境上相容之鹽型。合適之鹽通常為陽 離子之鹽類或酸之加成鹽類,該等陽離子或陰離子不會影 響活性成分之除莠作用。 合適之陽離子特定言之為鹼金屬之離子,較佳為鋰、鈉 與鉀之離子,鹼土金屬之離子,較佳為鈣與鎂之離子,及 過渡金屬之離子,較佳為錳、銅、鋅與鐵之離子,及銨, 此時若需要時,其中1至4個氫原子可被下列基團置換:a 一 C4-烷基、羥基燒基、CpCr燒氧基燒基、羥基_ CrQ-烷氧基-CrC4_垸基、苯基或苯甲基,較佳為銨、異丙 基知一甲基知、一兴丙基按、四甲基按、四丁基按、2_ (2-羥基乙小氧基)乙小基銨、二羥乙小基)銨、三甲基苯 甲基銨,及鱗離子、锍離子,較佳為三(CrCV烷基)锍及氧 化硫離子,較佳為三(Cl-C4_烷基)氧化锍。 合適之酸加成鹽之陰離子主要為氯離子、溴離子、氟離 子、硫酸氫根、硫酸根、磷酸二氫根、磷酸氫根、硝酸根 、碳酸氫根、碳酸根、六氟矽酸根、六氟磷酸根、苯甲酸 根,與CrCV烷酸之陰離子,較佳為甲酸根、乙酸根、丙酸 根與丁酸根。 較通合根據本發明混合物之協同除莠作用者為式j 3_雜環 基-取代之苯甲醯基衍生物,其中代號如下文中定義(不論 單獨或組合均適用): R 為由素如··氯或溴、CrCV烷基如:甲基或乙基或CrC6-86907 -26- 200410634 坑續g藍基如·甲%驢基或乙續醯基; 尤其佳為氯、甲基或甲磺醯基; R2 為選自下列之雜環基:異吟唑-3-基、豈崎岐:基與4’ 八 济下列 二氫異崎也-3-基,上述三個基團可未經取代戒、纟> / 基團取代單次或多次:鹵素、CrCV燒基、Ci-Cr嫁氧基 、CrC4- iS 基、CrC4-自垸氧基或crc4-燒减> 暴’ ^ 尤其佳為兴口号口圭** 5_基、3-甲基-異u号口坐_ ^基、 呤唑-3-基、5-甲基-4,5-二氫異噚唑-基、5-乙基-4,5*"〆氣 異嘮唑-3-基或4,5_二甲基_4,5_二氫異号嗤-基; r3為南素如··氯或溴或CrC6-烷磺醯基如··甲磺醯基或乙 磺醯基; 尤其佳為氯、甲續酸基或乙續醯基; R4 為氫或甲基; 尤其佳為氫; R 為Ci-C6-坑基,如:甲基、乙基、丙基、卜甲基乙基、 丁基、1-甲基丙基或孓甲基丙基; 籲 尤其佳為甲基、乙基或1-甲基乙基; R6為氫或CrCV垸基,如··甲基或乙基; 尤其佳為氫或甲基; - 極特別佳為彼等式Ia 3-雜環基_取代之苯甲醯基衍生物, 特定T之下表1所示之化合物Ia l至Ia 47 :'' Allidochlorn n ρ 48, `` Ethyl-benzyl propyl propionate ^ 112 (^ 一 叩 -ethyl) '' ρ 38, '' chlorthiamid 1 ' ρ · 150, "diphenamid" ρ · 34, π methyl-flamprop_methyl ρ · 40, π fosamin π ρ · 232, '' Isaiah Isoxaben π ρ 42, π monalide ”ρ 32,11 naptalam n ρ 36, n pronamid '' ρ 34, '' must rot ( "bialaphos" ρ · 234, "glufosinate-ammonium n 234, πglyphosate" ρ. 232, π amitrol '' ρ. 254, Μ clopeprop '' ρ · 20, `` dichlorprop '' ρ_6, '丨 fenoprop' 'ρ. 8, π fluroxypyr' 'ρ · 156 , 'FMCPAn ρ · 4, nMCPB ”ρ · 8, π mecoprop” ρ · 6, “napropamide n ρ · 16”, “tridopyr” ρ · 154 "N chloramben" ρ · 28, n Dicamba '' ρ 26, n clomazone ρ 268, `` diflufenican '' ρ 42, π fluorochloridone ρ 266 , Π fluridone '' ρ · 156, `` asulam 1 '' ρ · 12, `` barban '' ρ_ 100, `` butylate '' ρ_106, "carbetamide 1 'ρ · 6, n chlorobufam" ρ · 100, "cycloate' · ρ · 108," desmedipham ) '' ρ · 104, 86907 -21-200410634 π di-allate '' ρ · 106 '" EPTC " ρ · 108, `` orbencarb' 'p. 112,' 'Pebulate' ρ · 106, `` phenisopham '' ρ118, π phenmedipham '' ρ104,, f propham ', ρ 100, `` sulfallate '' ρ 110, 丨 丨 terbucarb, ρ 102, `` tri-allate '' ρ 108, '' Bandung (Vemo late), ρ 108, ', acetochlor 1' ρ 48, `` alachlor ', ρ 46,' diethathyl-ethyl ' ρ 48, `` dimethachlor, ρ 50 ,,, metolachlor '' ρ 46, '' propachbr, 'ρ 44,' ' Grass (prynachlor) ''44, π terbuchlor', ρ 48 ,,, xylachlor 'ρ 52,' alloxydim ', ρ 260, ", Clethodim" ρ · 270, "doproxydim", ρ 268, ', trakoxydim 1' ρ 270, "Draben ( dalapon), ρ 212 ,, ethofhmesate "ρ 124, π benefin, ρ 54, 54, butralin, ρ 58 '' ' "Dinitramin" ρ · 56, "ethalfluralin" ρ · 60, "fluchloralin" ρ.54 ,, iS0pr0palin ,, ρ · 58, " Naselin nitralin) ρ · 58, "oryzalin" ρ · 60 ,, prodiamine "ρ · 62," profluralin "ρ · 54, π three Forint (trifluralin) ρ 54, dinoseb, ρ 128 ,, dino 128 acetate, " ρ 128, `` dinoterb '' ρ 128, ,, DNOCn ρ · 126 ,,, acifluorfen-sodium, 'ρ · 142,', adonifen "ρ · 146," bifenox "ρ · 140 ' π Chlomitrofen 1 'ρ 138, `` difenoxuron' 'ρ 76, `` fluorodifen' ', ρ 138,, ethyl ethyl Fen bait 11〇1 * (^ 如 (^ 11々1 ^ 1), '? .146 ,, "Lacfen (1 & 〇1 (^ 11),". 144, "Sodium defen (nitrofen)" 136 ,,, "nitrofluorfen" ρ 141, 86907 -22- 200410634 `` oxyfluorfen '' ρ · 140, 'cyperquat-chloride' ρ · 158, π difenzoquat-methylsulfate & quot ρ · 160, "diquat" ρ · 158, · 'paraquat-dichloride 11 ρ · 158, π benzthiazuron with toluol "p. 82, '' Buturon '' ρ 66, `` chlorobromuron '' ρ 72, `` chloroxuron '' ρ 76, n chlorotoluron ρ · 74, n cycluron · ρ 84, n dimeforon 88, f 'diuron n ρ 70, n ethidimuron n ρ · 86, π fenuron '· ρ · 64, π fluometuron' 'ρ 68, ff isoproturon ”ρ 80, π isouron '' ρ 88, "Karbutilate" ρ · 76, `` Linuron " p. 72, π Toluene p-methabenzthiazuron '' ρ · 82, `` Metroxuron '' 'ρ · 72, "Monolinuron" ρ 66, π Monuron "ρ 64, π Neburon · 1 ρ 72,' 丨 西 有Dragon (siduron) '1 ρ 68, ff tebuthiuron "ρ 86," trimeturon "ρ 64," isocarbamid "ρ 168, ff Imazamethapyr ”p_ 172,“ imazapyr ”ρ · 170,“ imazaquin 丨 ”ρ 170,“ imazethapyr ”ρ · 172, "methazole" ρ · 162, fft? Oxadiazon "ρ · 162," tridiphane 丨 f p. 266, "bromoxynil ff ρ · 148, "Ioninil" ρ · 148, π diclofop-methyl "ρ · 16, π ethylfenfenprop" (fenthiapropethyl) ρ · 20 " (Fluazifop-butyl ) ρ. 18, `` Maloxyfop-methyln ρ · 18, π isoxapyrifop '' ρ. 22, `` propaquizafop '' ρ · 24 , Π ethyl fast kill Pu @ 1 ^ & 1〇 £ 〇 卩 -ethyl) '' ρ · 20, π chlorofenac '' ρ 258, π methyl kefenpu 86907 -23-200410634 (chlorfenprop-methyl) '' ρ · 258, " chlóridazon '' ρ · 174, π maleic hydrazide 'f ρ · 162, 丨 norflurazon' 'ρ. 174,' pyridate '1 ρ · 176 ,, clopyralid,' ρ · 154, '' picloram " ρ · 154, π ethylchem "Chlorimuron-ethyl" ρ · 92, π gram sulphur energy (chlorsulfUron) π ρ · 92, "flazasulfliron π ρ · 96," metsulfliron-methyl " 'ρ. 92, `` Nisoni (11 to 0311 he): 011)' '卩 .96, "Methyl Sutron (3111 ^ 011161: 111'011-111 € 1:11; / 1)' 'Kou.92', `` triasulfUron '' ρ. 94 ,, ametryn, ρ 198, π atrazine n 188, π aziprotryne "ρ 206," cyanazine'f ρ 192, π Cyprazine " ρ · 192, π desmetryne "ρ · 200, π dipropetryn" ρ · 202, "Ethyl Egner 81 丨 1 ^丨 11 < & > 4) "卩 .208," Philippine killing net (1 ^ \ 32 丨 11〇1 ^) "9.208, π procyazine" ρ. 192, π prometone ) "Ρ · 196, π general measurement (pr〇metryn) n ρ 196, π general management (propazine) 1 'ρ, 188," secbumeton n ρ. 196, π (Simazine) ρ · 188, π simetryn n ρ · 196, "terbumeton" ρ · 204, π terbutryn 1 'ρ · 198, π Terbutylazine 11 ρ · 190, πtrietazine '' 188, `` ethiozine '' ρ 210, `` metamitron '' ρ · 206, "Metribuzin" ρ · 202, "gram "Bromacil" ρ 180, 'f lenacil' 1 ρ 180, `` terbacil 1 'ρ 180, `` benazolin' 'ρ 262 "Bensulide" ρ · 228, "Benfluor" ρ · 266, "Butamifos" ρ. 228, ", DCPA" ρ · 28, "'Dichlobenil'" ρ · 148, ', "endothal" ρ · 264, "mefluidide" ρ · 306, "pufferone 86907 -24- 200410634 (perfluidone) ρ 260, `` terbuchlor '' ρ 48);-" Global Herbicide Directory "first edition, 1994 (see` `oxadiargyl '' ρ · 96);-" European Directory of Agrochemical Products " Vol. 2-Herbicidesf,, 4th edition (see f 'Buminafos 11 p. 255). -'' The Pesticide Manual, 12th edition, 2000 (see `` bispyribac-sodium '') p. 97, florasulam ρ 420, `` cyclosulfamuron ) "ρ 217," pretilachlor "ρ 755). In addition, the compound "DEH-ld ^" is shown in European patent application EP-A 302 203. The compound "tepraloxydim" is described in DE-A 33 36 140; the compound "ethyl sinonton (cinidon- `` ethyl '' is described in DE-A 36 03 789. The compound? Fluorbentranil? Is described in EP-A 84 893. Other compounds are known from `` Brighton Crop Protection Conference-Weeds-1993 '' 'f (see `` thidiazimin' 'p_ 29,,' AC- 322140 ”ρ · 41,“ KIH-6127, ”ρ · 47,” ProsulflnOn ”, ρ53, ΠΚΙ-20-20Π ρ · 61,“ Metobenzuron ”" ρ · 67 ). Compound π (carfenstmle (CH-900) n is described in EP-A 332 133, compound N-[[[4-methoxy-6- (trifluoromethyl) -1,3,5 -Sangen-2-yl] amino] -carbonyl] -2- (trifluoromethylbenzenesulfonamide) is described in PCT / EP 96/03996. The active ingredients specified for each mechanism are based on current knowledge If an active ingredient is suitable for multiple mechanisms, this substance is only assigned to one mode of action. Formula I 3-Heterocyclyl-substituted benzamidine derivatives can be used as pure enantiomers or as Use as racemates or diastereoisomeric mixtures. 86907 25-200410634 Formula I 3-heterocyclyl-substituted benzamidine derivatives and / or compounds with a herbicidally active compound from group b and / or from C1SCi6 The tritium-removing active compound in the group can also be an environmentally compatible salt type. Suitable salts are usually cation salts or acid addition salts, and these cations or anions will not affect the tritium removal of the active ingredient. Suitable cations are specifically alkali metal ions, preferably lithium, sodium and potassium ions, alkaline earth metal ions, preferably calcium and Ions and transition metal ions, preferably ions of manganese, copper, zinc and iron, and ammonium, where 1 to 4 hydrogen atoms can be replaced by the following groups if necessary: a -C4-alkane Radical, hydroxyalkyl, CpCralkyl, hydroxy_CrQ-alkoxy-CrC4_fluorenyl, phenyl or benzyl, preferably ammonium, isopropyl, monomethyl, isopropyl Radical, tetramethyl radical, tetrabutyl radical, 2- (2-hydroxyethoxy) ethynyl ammonium, dihydroxyethynyl) ammonium, trimethylbenzyl ammonium, and scale ion, thallium ion Of these, tris (CrCV alkyl) scandium and sulfur oxide ions are preferred, and tris (Cl-C4_alkyl) scandium oxide is preferred. The anions of suitable acid addition salts are mainly chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, The anions of hexafluorophosphate, benzoate and CrCV alkanoic acid are preferably formate, acetate, propionate and butyrate. A more general synergist of the mixtures according to the present invention is the formula j 3_heterocyclyl-substituted benzamidine derivatives, wherein the symbol is as defined below (either alone or in combination): R is represented by ·· Chlorine or bromine, CrCV alkyl such as: methyl or ethyl or CrC6-86907 -26- 200410634 Hanging g blue group such as · %% donkey or ethyl fluorenyl; particularly preferably chlorine, methyl or methyl Sulfofluorenyl; R2 is a heterocyclic group selected from the group consisting of isoxazol-3-yl, akizaki: and the following dihydroisozaki-3-yl group of 4′-Bachi, the above three groups may not be Substitution or 纟 > / group substitution one or more times: halogen, CrCV alkyl, Ci-Cr alkyloxy, CrC4- iS group, CrC4- autofluorinated or crc4- burned > ^ Especially preferred is the slogan of Xing ** 5-yl, 3-methyl-iso-u slogan ^ ^, pyridazol-3-yl, 5-methyl-4,5-dihydroisoxazole- Group, 5-ethyl-4,5 * " fluorene isoxazol-3-yl or 4,5_dimethyl_4,5_dihydroisofluorene fluorenyl-group; r3 is Nansu such as ·· Chlorine or bromine or CrC6-alkanesulfonyl groups such as methylsulfonyl or ethylsulfonyl; particularly preferred are chlorine, methylidene or ethylidene; R4 Hydrogen or methyl; particularly preferred is hydrogen; R is Ci-C6-pit, such as: methyl, ethyl, propyl, methyl ethyl, butyl, 1-methylpropyl, or methylmethylpropyl; Particularly preferred is methyl, ethyl or 1-methylethyl; R6 is hydrogen or CrCV 垸, such as methyl or ethyl; particularly preferred is hydrogen or methyl;-very particularly preferred is their formula Ia 3-heterocyclyl-substituted benzamidine derivatives, compounds Ia l to Ia 47 shown in Table 1 below specific T:
86907 27- 20041063486907 27- 200410634
No. R1 R2-- R3 R4 R5 R6 Ia.l τ Cl 4,5-—氫異崎唾-3-基 so2ch3 H ch3 ch3 la.2 Cl 4,5-二氫異吟唑_3-基 Cl H ch3 ch3 Ia.3 Cl 4,5_ 一氫異噚唑-3-基 so2ch3 H ch3 H Ia.4 Cl 4,5-—氫甲基異ρ号峻-3-基 S02CH3 H ch3 H Ia.5 Cl 二甲基異嘮唑_3-基 so2ch3 H ch3 H Ia.6 Cl 二美-3-乙基異ρ咢η坐-3-基 S02CH3 H ch3 H Ia.7 Cl 4’5-一鐵γ5,5-二乙基異ρ号峻_3-基 so2ch3 H ch3 H Ia.8 Cl 氯甲基異嘮唑-3-某 so2ch3 H CH. H Ia.9 Cl 乙氧基異π咢吨-3-基 so2ch3 H ch3 H la. 10 Cl 4’5-一氫-5-甲氧基異号峻-3-基 S02CH3 H CH. H la. 11 Cl 二甲基異嘮唑_3 一基 S02CH3 H ch3 H la. 12 Cl 4,5-一虱-5-硫乙基異基 so2ch3 H ch3 H la. 13 Cl 三氟甲基異呤唑各某 so2ch3 H ch3 H la. 14 Cl 4,5_—IL 異 4 峻-3-基 so2ch3 H c2h. H la. 15 Cl 4,5_—氫異 4^-3-基 Cl H ^ZA AJ C9EU H la. 16 Cl ^^4:5-甲基異吟唑-3-基 S02CH3 H H la. 17 Cl 二甲基異噚唑-3-某 S02CH3 H xj C0H5 H la. 18 Cl 4,5· 一氫乙基異嘮唑_3_基 so2ch3 H C9H. H la. 19 Cl 二乙基異呤唑_3-某 S02CH3 H C2Hs H Ia.20 Cl 氯甲基異噚唑各某 S02CH3 H C9H5 H Ia.21 Cl 4,5-—氫異呤唑-3-基 SOCH3 H C?H. H Ia.22 Cl 乙氧基異吟唑各某 S02CH3 H XJ CoH. H Ia.23 Cl 二甲基異嘮唑-3-^ S02CH3 H X-/ZX xj C9Hs H Ia.24 Cl 4,5-*—氫4-¾乙基異5冲-V基 S02CH3 H ^Zx XJ C9H5 H Ia.25 Cl 三氟甲基異呤唑-31 S02CH3 H C9H. H Ia.26 Cl 4,5-一氫異噚唑各基 S02CH3 H v-^zx XJ 1-C4H9 H Ia.27 ch3 4,>一風異呀17坐-3-基 so2ch3 H CH. ch3 Ia.28 ch3 4,5_—氫異号唑_3_基 Cl H CHU CHU Ia.29 ch3 4,5_—氫異崎唾_3_基 S02CH3 H ch3 A3 H Ia.30 CH3 4,5·一氫_5_甲基異口号口坐_3-基 S02CH3 H ch3 H Ia.31 ch3 二甲基異噚唑各基 S02CH3 H ch3 H Ia.32 ch3 4,5-—氫_5_乙基異崎峻_3_基 S02CH3 H ch3 H Ia.33 CH3 二乙基異噚吨_3-其 S02CH3 H CHU H Ia.34 ch3 4,5_ 一氫異呤唑各基 S02CH3 H Aj CH. H Ia.35 ch3 4,5-一氫_4,5-二甲基異噚唑|其 S02CH3 H WA Aj ch3 H 86907 -28- 200410634No. R1 R2-- R3 R4 R5 R6 Ia.l τ Cl 4,5-—Hydrazine-3-yl so2ch3 H ch3 ch3 la.2 Cl 4,5-Dihydroisoindazole_3-yl Cl H ch3 ch3 Ia.3 Cl 4,5_ monohydroisoxazol-3-yl so2ch3 H ch3 H Ia.4 Cl 4,5 --- hydromethylisoiso-3-ol S02CH3 H ch3 H Ia.5 Cl dimethylisoxazole_3-ylso2ch3 H ch3 H Ia.6 Cl dime-3-ethylisoρ 咢 η sitting-3-yl S02CH3 H ch3 H Ia.7 Cl 4'5-monoferric γ5 , 5-Diethylisoρ 号 Jun_3-yl so2ch3 H ch3 H Ia.8 Cl Chloromethylisoxazole-3-So2ch3 H CH. H Ia.9 Cl Ethoxyisopropion ton-3 -Group so2ch3 H ch3 H la. 10 Cl 4'5-monohydro-5-methoxyisopropyljun-3-yl S02CH3 H CH. H la. 11 Cl dimethylisoxazole_3 mono S02CH3 H ch3 H la. 12 Cl 4,5-monolice-5-thioethylisoyl so2ch3 H ch3 H la. 13 Cl trifluoromethylisopurazol each so2ch3 H ch3 H la. 14 Cl 4,5_-IL Iso4 Jun-3-yl so2ch3 H c2h. H la. 15 Cl 4,5_-hydroiso 4 ^ -3-yl Cl H ^ ZA AJ C9EU H la. 16 Cl ^^ 4: 5-methylisoindazole -3-yl S02CH3 HH la. 17 Cl dimethylisoxazole 3-S02CH3 H xj C0H5 H la. 18 Cl 4,5 · monohydroethylisoxazole_3_yl s o2ch3 H C9H. H la. 19 Cl Diethylisopurazol_3-S02CH3 H C2Hs H Ia.20 Cl Chloromethylisoxazole S02CH3 H C9H5 H Ia.21 Cl 4,5 --- Hydroxyiso Pyrazol-3-yl SOCH3 HC? H. H Ia.22 Cl Ethoxyisoindazole S02CH3 H XJ CoH. H Ia.23 Cl Dimethylisoxazole-3- ^ S02CH3 H X- / ZX xj C9Hs H Ia.24 Cl 4,5-*-hydro 4-Ethylisopentyl-5V-S02CH3 H ^ Zx XJ C9H5 H Ia.25 Cl Trifluoromethylisopurazol-31 S02CH3 H C9H. H Ia.26 Cl 4,5-monohydroisoxazolyl radicals S02CH3 H v- ^ zx XJ 1-C4H9 H Ia.27 ch3 4, > Yifengyiya 17-syn-3-so2ch3 H CH. Ch3 Ia .28 ch3 4,5_-hydroisoxazole_3_yl Cl H CHU CHU Ia. 29 ch3 4,5 _-- hydroisozyl_3_yl S02CH3 H ch3 A3 H Ia.30 CH3 4,5 · monohydrogen _5_methylisoslogan slogan_3-yl S02CH3 H ch3 H Ia.31 ch3 dimethylisoxazole groups Jun_3_S02CH3 H ch3 H Ia.33 CH3 Diethylisoxanthene_3-its S02CH3 H CHU H Ia.34 ch3 4,5_ monohydroisoxazolyl groups S02CH3 H Aj CH. H Ia.35 ch3 4,5-monohydro_4,5-dimethylisoxazole | its S02CH3 H WA Aj ch3 H 86907 -28- 20041 0634
Xb 亦極特別佳為式Ic化合物,特定言之化合物Ι(λ1至Ic 47 ,其與化合物Ia.l至Ia.47之差異僅在於其係呈鋰鹽:Xb is also very particularly preferably a compound of formula Ic, specifically compound I (λ1 to Ic 47, which differs from compounds Ia.l to Ia.47 only in that it is a lithium salt:
Ra R3 亦極特別佳為式Id化合物,特定言之化合物Id.l至Id.47 ,其與化合物Ia.l至Ia.47之差異僅在於其係呈鉀鹽:Ra R3 is also very particularly a compound of formula Id, specifically compounds Id.l to Id.47, which differ from compounds Ia.l to Ia.47 only in that they are potassium salts:
R2 R3R2 R3
Id 亦極特別佳為式Ie化合物’特定言之化合物Ie.l至Ie_47 86907 -29- 200410634 按鹽 其與化合物1a·1至1a.47之差異僅在於其係呈Id is also very particularly a compound of the formula Ie ’, specifically the compounds Ie.l to Ie_47 86907 -29- 200410634, which differ from the compounds 1a · 1 to 1a.47 by salt only in that they present
R1 le 卜極特別佳為式I 3-雜環基_取代之苯甲醯基衍生 物,其中 R4為氫。 彳―特別佳為式I 3-雜環基_取代之苯甲醯基衍生 物,其中 、 歹】之旅環基:異4吐-3-基、異4嗤_4_基盘 異口咢唆·5_其,、— 〆、 土 上述三個基團可未經取代或經下列基 團取代單次咬容☆ . &主 ^ 基、 及夕次· _素、CrC4-烷基、CrCr烷氧 打南燒基、Cl_Q·卣燒氧基或Cl_C4-燒硫基。 極特別佳為式τ 中 雖環基-取代之苯甲醯基衍生物,其 R為可未經取代 . 八或經下列基團取代單次或多次之異喝 1 -心基:鹵去 燒其、 、1、CrCr烷基、CrC4-烷氧基、CrC4-鹵 R4為氫。Cl<:4,烷氧基或CrCV垸硫基; 1 1雜環基-取代之苯甲醯基衍生物, 極特別佳亦為式 其中 86907 R2為可未經取代或 口至4基: 南素、 經下列基團取代單次或多次之異呤 CKV烷基、cr(V^氧基、CKV鹵 -30- 200410634 燒基、CrCV _燒氧基或cvcv燒硫基; R為氯。 最特別佳亦A 4「9 # ,/ 為乳4(3-甲基-異哼唑-5-基)-‘甲旙醯 基-苯甲醯基M-甲A n山I τ /、 丫卷5»技基-iH-p比。坐。 取特別佳亦為4-[2一甲基邻-甲基-異十坐-5-基)-4-甲續醯 基-苯甲基]-1呷基_5邊基_1H_吡唑。 卜極特別佳為式I 3-雜環基-取代之苯甲醯基衍生 物,其中 R2為選自下列之雜環基·· 4,5-二氫異嘮唑-3-基、4>二 氫異碭唑-4-基與4,5_二氫異呤唑基,上述三個基 團可未經取代或經下列基團取代單次或多次··鹵素 Ci C4烷基、crC4-烷氧基、crC4-ii烷基、crC4-鹵 坑氧基或CrC4-燒硫基。 極特別佳為式I 3-雜環基-取代之苯甲醯基衍生物,並 中 〃 R為可未經取代或經下列基團取代單次或多次之4,5_ 一氫異5唑-3-基:_素、CrCV烷基、Cl-C4烷氧基、 CrCV自烷基、Q-cv _烷氧基或c^—烷硫基; R為氫。 最特別佳亦為式I 3-雜環基_取代之笨甲醯基衍生物, 其中R1 le is particularly preferably a 3-heterocyclyl-substituted benzamidine derivative of formula I, wherein R4 is hydrogen.彳-particularly preferred is a 3-heterocyclyl_substituted benzamidine derivative of formula I, in which, 歹] travel ring groups: iso-4-pent-3-yl, iso-4 嗤 -4_base唆 · 5_ Which ,, 〆, and the above-mentioned three groups may be unsubstituted or substituted by the following groups for a single occlusion ☆. &Amp; the main group, and the base group, CrC4-alkyl, CrCr alkoxy benzyl, Cl_Q · fluorenyloxy or Cl_C4-sulfanyl. Very particular preference is given to the ring-substituted benzamidine derivative of formula τ, where R is unsubstituted. Eight or one or more substitutions of 1-cardio: halogenation Burning it, 1, 1, CrCr alkyl, CrC4-alkoxy, CrC4-halo R4 is hydrogen. Cl <: 4, alkoxy or CrCV sulfanyl; 1 1 heterocyclyl-substituted benzamidine derivatives, very particularly also of the formula wherein 86907 R2 is unsubstituted or substituted to 4 radicals: South A single or multiple isocyanate CKV alkyl group, cr (V ^ oxy group, CKV halo-30-200410634 alkyl group, CrCV_alkyloxy group or cvcv alkylthio group are substituted by the following groups; R is chlorine. The most particularly good is A 4 "9 #, / is milk 4 (3-methyl-isohumazol-5-yl)-'methylamidino-benzylidene M-methyl A n I / / Volume 5 »Technical base-iH-p ratio. Sitting. Especially preferred is also 4- [2-methyl-o-methyl-isodecyl-5-yl) -4-methylcontinyl-benzyl] -1fluorenyl_5side group_1H_pyrazole. Particularly preferred is a 3-heterocyclyl-substituted benzamidine derivative of formula I, wherein R2 is a heterocyclic group selected from the group consisting of 4, 5-dihydroisoxazol-3-yl, 4 > dihydroisoxazol-4-yl and 4,5-dihydroisopyrazolyl, the above three groups may be unsubstituted or substituted with the following groups Single or multiple times. Halogen Ci C4 alkyl, crC4-alkoxy, crC4-ii alkyl, crC4-halooxy or CrC4-sulfanyl. Very particular preference is given to the formula I 3-heterocyclyl- Substituted benzamidine Derivatives, in which R is a 4,5_ monohydroiso5azol-3-yl group that may be substituted unsubstituted or substituted one or more times by the following groups: 素 prime, CrCV alkyl, Cl-C4 alkoxy CrCV is from alkyl, Q-cv_alkoxy or c ^ -alkylthio; R is hydrogen. Most particularly preferred is also a 3-heterocyclyl-substituted benzamidine derivative of formula I, wherein
Rl為_素或CrC6-烷基;及 圮為可未經取代或經下列基團取代單次或多次之4,5_ 一氫異5哇-3-基:_素、CVC4、烷基、CrCr烷氧基 86907 -31- 200410634 、CpCrii烷基、CrCpii烷氧基或CrC4-烷硫基; R3為Ci-C6-燒續驗基, R4為氫。 最特別佳為4-[2-氯·3-(4,5-二氫異呤唑-3-基)-4-甲磺醯基-苯甲醯基]-1_甲基-5-羥基-1H-吡唑。 最特別佳亦為4-[2-甲基-3-(4,5-二氫異噚唑-3-基)-4-甲磺 醯基-苯甲醯基]-1-甲基-5-羥基-1H-吡唑。 根據本發明混合物之協同除莠作用較佳方面為彼等包含 依滅草(imazapyr)與依滅特(imazethapyr)、或依滅草(imazapyr)與 依滅比(imazapic)作為成分B)之混合物,尤指包含依滅草 (imazapyr)與依滅特(imazethapyr)作為成分B)之混合物。 另一項較佳方面,協同除莠混合物包含三種除莠活性化 合物:式I化合物(成分A)與兩種選自下列各物組成之群中 之除莠劑:依滅草(imazapyr)、依滅克(imazaquin)、甲基依滅本 (imazamethabenz-methyl)、依滅莫(imazamox)、依滅比(imazapic)與 依滅特(imazethapyr)(成分 B)。 - 特別佳具體實施例中,上述各較佳具體實施例亦同樣 適用。 特定言之,協同除莠混合物包含作為成分A之4-[2-甲基-3-(4,5-二氫異噚唑-3-基)-4-甲磺醯基-苯甲醯基]-1-甲基-5-經基-lH-ρ比峻與兩種選自下列各物組成之群中之除莠 劑:依滅草(imazapyr)、依滅克(imazaquin)、甲基依滅本 (imazamethabenz-methyl)、依滅莫(imazamox)、依滅比(imazapic) 與依滅特(imazethapyr)(成分B)。 86907 -32- 200410634 尤其佳之協同除莠混合物包含作為成分A之4-[2-甲基-3- - (4,5-二氫異噚唑-3-基)-4-甲磺醯基-苯甲醯基]-1-甲基-5-經基-1Η-ρ比吐與作為成分B)之依滅草(imazapyr)與依滅特 (imazethapyr) 〇 另一項具體實施例中,協同除莠混合物包含作為成分 A之4-[2-甲基- 3-(4,5-二鼠異1:7号口坐-3-基)-4-甲績驗基-苯甲 醯基]-1-甲基-5-羥基-1H-吡唑與作為成分B)之依滅草 (imazapyr)與依滅比(imazapic)。 鲁 另一項較佳具體實施例中,協同除莠混合物包含至少四 種除莠活性化合物:式I化合物(成分A)、兩種選自下列各物 組成之群中之除莠劑:依滅草(imazapyr)、依滅克(imazaquin)、 甲基依滅本(imazamethabenz-methyl)、依滅莫(imazamox)、依滅 比(imazapic)與依滅特(imazethapyr)(成分 B)與 C) 至少一種選自下列之除莠化合物:乙醯基CoA羧化酶 抑制劑(ACC)、乙醯基乳酸酯合成酶抑制劑(ALS)、醯胺 類、植物生長素除莠劑、植物生長素運輸抑制劑、類 ® 胡蘿蔔素生合成抑制劑、烯醇丙酮基莽草酸3-磷酸酯 合成酶抑制劑(EPSPS)、麩醯胺合成酶抑制劑、脂質生 合成抑制劑、有絲***抑制劑、原W、p林原IX氧化酶抑 制劑、光合作用抑制劑、協同製劑、生長物質、細胞 壁生合成抑制劑及其他多種除莠劑。 基於包含根據本發明成分A)、B)與C)之混合物之協同 除莠作用之觀點,最好以選自C1至C14或C16族群中之 化合物作為成分C),較佳為選自C9與C12族群。 86907 -33- 200410634 特定言之,以選自下文所述之活性成分種類中之化合 _ 物較佳,或以下列化合物極特別佳: C1乙醯基CoA羧化酶抑制劑(ACC): -環己烯酮Μ酸類,特定言之:赛克定(cycloxydim) 、希特定(sethoxydim)或三克定(tralkoxydim),較佳為 希特定(sethoxydim)或三克定(tralkoxydim);或 -苯氧苯氧丙酸酯類,特定言之:炔丙基克丁弗 (clodinafop-propargyl)(及若適當時,克昆赛(cloquintocet)) Φ 、乙基芬諾普(fenoxaprop-ethyl)或P-乙基芬锘普,較 佳為块丙基克丁弗(clodinafop-propargyl)(及若適當時 ,克昆赛(cloquintocet))或P-乙基芬諾普; C2乙醯基乳酸酯合成酶抑制劑(ALS): -咪峻淋酮類,特定言之:依滅草(imazapyr)、依滅克 (imazaquin)、依滅本(imazamethabenz)、依滅特(imazethapyr) 或依滅莫(imazamox),較佳為依滅草(imazapyr); -响咬基醚類(pyrimidyl ethers),特定言之·· p比硫貝酸拳 鋼(pyrithiobac sodium); -續酿胺類,特定言之:伏速爛(florasulam)、滅速爛 (flumetsulam)或特速爛(metosulam),較佳為特速爛 (metosulam);或 -續S盛基脲類,特定言之:甲基賀速能(halosulfliron-methyl)、尼速能(nicosulfUron)、甲基普速能(primisulfuron· methyl)、普洛速能(prosulfUron)、靈速能(rimsulfhron) 、甲基地芬速能(thifensulforon-methyl)、甲基三本能 86907 -34 - 200410634 (tribenuron-methyl)、N-[[[4-甲氧基-6-(三氟甲基)-l,3,5-三畊-2-基]-胺基]羰基]-2-(三氟甲基)-苯磺醯胺或 績速能(sulfosulfuron); C3醯胺類: -伏赛滅(fluthiamide); C4植物生長素除莠劑: -吡啶羧酸類,特定言之:陶斯松(clopyralid);或 -2,4-D ; C5植物生長素運輸抑制劑: -大芬比(diflufenzopyr); C6類胡蘿蔔素生合成抑制劑: -艾弗特(isoxaflutole)、滅奇酮(mesotrione)、艾氯得 (isoxachloride)、奇特斯(ketospiradox)或速克酮(sulcotrione (chlormesulone)),特定言之艾弗特(isoxaflutole)或速 克酉同(sulcotrione); C7烯醇丙酮基莽草酸-3-磷酸酯合成酶抑制劑(EPSPS): -草甘膦(glyphosate)或弗赛(sulfosate); C8麩醯胺合成酶抑制劑: _ 古弗辛铵(glufosinate-ammonium); C9脂質生合成抑制劑: -氯乙醯替苯胺,特定言之:大滅醯胺(dimethenamid)、 S-大滅醯胺、乙醯拉草(acetochlor)、滅多草 (metolachlor)或 S-滅多草; -硫脲類(thioureas),特定言之:殺丹(benthiocarb); 86907 -35- C10有絲***抑制劑: 一一硝基苯胺類,特定言之··施得圃(pendimethalin); C11原卟啉原〗义氧化酶抑制劑: •—苯基醚類,特定言之:亞喜芬(acifluorfen)或亞 喜芬鈉; -’二唾類,特定言之:樂得奇(oxadiargyl);或 -環狀亞胺類,特定言之:布塔芬(butafenacil)、乙 基卡芬松(carfentrazone-ethyl)、乙基辛尼頓(cinidon-ethyl)或戊基弗克拉(flumiclorac-pentyl),較佳為乙基 卡芬松(carfentrazone-ethyl)、乙基辛尼頓(cinidon-ethyl) 或戊基弗克拉(flumidorac-pentyl); -吡唑類,特定言之JV 85 ; C12光合作用抑制劑: -必汰草(pyridate)或必達伏(pyridafol),特定言之必汰 草(pyridate); -苯並p塞二喷酮類,特定言之本達隆(bentazone); -二伸p比淀類,特定言之:巴拉刘二氯化物(paraquat-dichloride); -脲類,特定言之:達有龍(diuron)或異普特能 (isoproturon),較佳為達有龍(diuron); -苯驗類,特定言之:溴尼(bromoxynil); -克達松(chloridazone); -三命類,特定言之草脫淨(atrazine)或脫別淨 (terbutylazine);或 86907 -36- 200410634 -三p井酮類,特定言之:滅必淨(metribuzin); C13協同製劑: -環氧乙燒類,特定言之:三地芬(tridiphane); C14生長物質: -芳氧燒酸類,特定言之:氟氯比(fluoroxypyr)、 MCPA 或滅克普-P(mecoprop-P); -苯甲酸類,特定言之:汰克草(dicamba);或 -口奎琳致酸類,特定言之:快克拉(quinclorac); C16其他多種除莠劑: -三亞凡(triaziflam)。 特定言之,以選自下文所述之活性成分種類中之化合物 較佳,或以下列化合物極特別佳: C9脂質生合成抑制劑: -氣乙縫替苯胺,特定言之:大滅酸胺(dimethenamid) 、S-大滅驢胺、乙驢拉草(acetochlor)、滅多草 (metolachlor)或 S-滅多草; C12光合作用抑制劑: -必汰草(pyridate); 苯並卩塞二ρ井酮類,特定言之:本達隆(bentazone); -二伸p比症類,特定言之:巴拉刈二氯化物(paraquat-dichloride); -脲類,特定言之:達有龍(diuron)或異普特能 (isoproturon),以達有龍(diuron)較佳; -苯齡類,特定言之:溴尼(bromoxynil); 86907 -37- 200410634 -克達松(chloridazon); -三畊類,特定言之:草脫淨(atrazine)或脫別淨 (terbutylazine);或 -三p井酮類,特定言之:滅必淨(metribuzin) 〇 特別佳具體實施例中,上述各較佳具體實施例亦同樣適 用。 尤其佳之協同除莠混合物包含作為成分A之4-[2-甲基-3-(4,5-二氫異崎唑-3-基)-4-甲磺醯基-苯甲醯基]-1-甲基-5-羥基· 鲁 1H-吡唑;作為成分B之兩種選自下列各物組成之群中之除 莠劑:依滅草(imazapyr)、依滅克(imazaquin)、甲基依滅本 (imazamethabenz-methyl)、依滅莫(imazamox)、依滅 t匕(imazapic)與 依滅特(imazethapyr);與作為成分C之選自C9族群中之除莠化 合物,特定言之氯乙醯替苯胺,尤指乙醯拉草(acetochlor)。 特別佳之協同除莠混合物包含作為成分A之4-[2-甲基-3-(4,5-二氮異p号吐-3-基)-4-甲續酸基-苯甲酸基]-1-甲基-5-輕基-1H-峨η坐;作為成分B之依滅草(imazapyr)與依滅特(imazethapyr) 鲁 ,與作為成分C之氯乙驗替苯胺’尤指乙驢拉草(acetochlor)。 特別佳之協同除莠混合物包含作為成分A之4-[2-甲基-3-(4,5-二氫異η号吐-3-基)-4-甲續醯基-苯甲驢基]-1-甲基_5_輕基-1H-吡唑;作為成分B之依滅草(imazapyr)與依滅比(imazapic);與 作為成分C之氯乙醯替苯胺,尤指乙醯拉草(acet〇chl〇r)。 亦尤其佳之協同除莠混合物包含作為成分A之4-[2-甲基-3-(4,5-二氫異4咬-3-基)-4-甲績酸基-苯甲醯基]甲基樂基-1H-吡唑、作為成分B之兩種選自下列各物組成之群中之除 86907 -38- 200410634 莠劑:依滅草(imazapyr)、依滅克(imazaquin)、甲基依滅本 (imazamethabenz-methyl)、依滅莫(imazamox)、依滅比(imazapic)與 依滅特(imazethapyr);與作為成分C之選自C12族群中之除莠 化合物,特定言之三p井類,尤指草脫淨(atrazine)或苯並p塞二 喷酮類,尤指本達隆(bentazone)。 特別佳之協同除莠混合物包含作為成分A之4-[2-甲基-3-(4,5-二鼠異4 0坐-3-基)-4-甲續驢基-苯甲酿基]-1-甲基-5-蠢基-lHw比咬;作為成分B之依滅草(imazapyr)與依滅特(imazethapyr) •,與作為成分C之三p井類,尤指草脫淨(atrazine)。 特別佳之協同除莠混合物包含作為成分A之4-[2-甲基-3-(4,5-二氫異呤唑-3-基)-4-甲磺醯基-苯甲醯基]-1-曱基-5-羥基-1Η-ρ比吐;作為成分B之依滅草(imazapyr)與依滅特(imazethapyr) •,與作為成分C之苯並p塞二π井酮類,尤指本達隆(bentazone)。 特別佳之協同除莠混合物包含作為成分A之4-[2-甲基-3-(4,5-二氫異哼唑-3-基)-4-曱磺醯基-苯甲醯基]-1-甲基-5-羥基-1H-口比口坐;作為成分B之依滅草(imazapyr)與依滅比(imazapic); 與作為成分C之三畊類,尤指草脫淨(atrazine)。 特別佳之協同除莠混合物包含作為成分A之4-[2-甲基-3-(4,5-二氮異亏17坐-3-基)-4-甲績6盔基-苯甲酸基]-1-甲基-5-經基-lH-ρ比吐;作為成分B之依滅草(imazapyr)與依滅比(imazapic); 與作為成分C之苯並p塞二p井嗣類,尤指本達隆(bentazone)。 本發明亦延伸至一種除莠組合物,其包含除莠活性量之 協同除莠混合物(其包含如上述之成分A)、B)與若需要時使 用之C))、至少一種液態與/或固態載劑及若需要時使用之 86907 -39- 200410634 至少一種界面活性劑。 根據本發明除莠組合物與協同除莠混合物對作物(如:玉 米、穀類、稻與大豆)中之闊葉雜草與草本雜草具有極佳控 制效果,但不會傷害作物植株,尤其在極低施用率下仍可 見到此效果。 根據本發明除莠組合物與協同除莠混合物可考量多種不 同施用法亦用於其他多種作物植株上,以消除不要之植物 。合適作物實例如下:慧(Allium cepa)、鳳梨(Ananas comosus)、 落花生(Arachis hypogaea)、蘆筍(Asparagus officinalis)、蒸菜(Beta vulgaria ssp· altissima、Beta vulgaria ssp· rapa)、蕓苔(Brassica napus var· napus、Brasaica napus var· napobrassica、Brassica rapa var· silvestris)、山 茶(Camellia sinensis) 、I工花(Carthamus tinctorius)、山核才兆(Carya illinoinensis)、擰檬(Citrus limon)、掛橘(Citrus sinensis)、咖啡(Coffea arabica)(Coffea canephora、Coffea liberica)、甜瓜(Cucumis sativus)、狗 牙根(Cynodon dactylon)、胡蘿蔔(Daucus carota)、油椰子(Elaeis guineensis)、蛇莓(Fragaria vesca)、大豆(Glycine max)、棉(Gossypium hirsuUim)(Gossypium arboreum 'Gossypiumherbaceum ^Gossypium vitifolium) 、向曰葵(Helianthua annuus)、巴西橡膠樹(Hevea brasiliensis)、大麥 (Hordeum vulgare)、啤酒花(Humulus lupulus)、甘藷(Ipomoea batatas)、胡桃(Juglans regia)、靈視豆(Lens culinaris)、亞麻(Linum usitatissimum)、番痴(Lycopersicon lycopersicum)、蘋果(Malus spp.) 、白附子(Manihot esculenta)、苜蓿(Medicago sativa)、芭蕉(Musa spp·)、芬草(Nicotiana tabacum)(N. rustica)、歐洲橄檀(Olea europaea) 、稻(Oryza sativa)、菜豆(Phaseolus lunatus、Phaseolus vulgaris)、雲 86907 -40- 200410634 杉(Picea abies)、松(Pinus spp.)、碗豆(Pisum sativum)、梅(Pmnus — avium)、樓(Primus persica)、梨(Pyrus communis)、酷栗(Ribes sylvestre)、蓖麻(Ricinus communis)、甘廉(Saccharum officinarum)、 黑麥(Secale cereale)、% (Solanum tuberosum)、高粱(Sorghum bicolor) (S.vulgare)、可可;f封(Theobroma cacao)、三葉草(Trifolium pratense) 、小麥(Triticum aestivum)、硬粒小麥(Triticum durum)、蠶豆(Vicia faba)、葡萄(Vitis vinifera)與玉米(Zea mays)。 此外,根據本發明除莠組合物與協同除莠混合物亦可用 鲁 於因育種(包括基因工程法)而耐受除莠劑作用之作物。 根據本發明混合物或含其之除莠組合物可呈例如:可直 接噴麗之水溶液、散劑、懸浮液、及高濃度之水性、油性 或其他懸浮液或勻散液、乳液、油勻散液、糊劑、細粉劑 、撒播材料或粒劑等型式,利用喷灑、氣霧化、撒粉、撒 播或傾倒等方式使用。 其使用型式依所計畫之目的而定;任何情況下均應確保 根據本發明活性成分可均勻分佈。 籲 合適之惰性輔劑為中沸點至高沸點之礦物油餾份,如: 煤油與柴油,及煤焦油與植物油或動物油,脂系、環系及 芳香系烴類,例如:石蠟、四氫莕、烷基化莕及其衍生物 ,烷基化苯及其衍生物,醇類如:甲醇、乙醇、丙醇、丁 醇與環己醇,酮類如:環己酮,強極性溶劑,如:N-甲基 口比洛燒酮及水。 水性施用形式可由乳液濃縮物、懸浮液、糊劑、可濕化 散劑或水可勻散性粒劑加水製得。製備乳液、糊劑或油勻 86907 -41 - 200410634 ::時’物質呈其本身或溶於油或溶劑中後,於水令利用 ::劑' 膠黏劑、勾散劑或乳化劑均質化。然而,亦可製 =性物質、濕化劑、膠黏劑、句散劑或乳化劑,及若 =使用之溶劑或油組成之濃縮物,此等濃縮物適合加 之界面活性劑為:驗金屬、龄土金輪之芳香手 =:二如:木質素續酸鹽、苯嶋鹽、㉔酸鹽與 一"丁基秦石頁酸鹽,於输 L、 燒A離二貌基-與垸芳基-續酸鹽, 土力L h,月桂基醚硫酸鹽, 化十六垸醇’十七垸醇與十八垸醇=%硫酸鹽,及硫酸 茶及其衍生物與甲駿之、•合產物,㈠ 奈㈣類與苯紛及甲駿之縮合產物 ”戈 類,乙氧化異辛基齡,乙氧 、t市辛土丰基醚 苯基聚二醇醚類, 4或乙氧化壬基鼢,烷 類,異十三燒基醇,月氷二_類,燒芳基聚趟醇 油,聚氧乙缔燒基二,乙氧化萬麻 二醇醚乙酸酯,山利棘砬 、布I基醚類,月桂基醇聚 基纖維素。 木貝素亞硫酸鹽廢液或甲 製備散劑’撤播材料逝*、,、 或個別活性成分逝固能 知训時,可使協同除莠混合物 製備粒劑,例如:::m共同研磨。 可使活性成分與固態載2,反泡粒劑與均質粒劑時, 石、矽膠、矽酸鹽、、^固怨載劑為礦物土如:矽 、膠塊黏土、黃土、黏土回,土、石灰石、石灰、白堊 白雲石、矽藻土、硫酸鈣、硫 86907 -42- :氧化鎂、合成物磨粉、肥料如:硫酸銨、磷酸銨、 :了 I素、及植物性產物如:穀粉、樹皮粉、木材粉 1挪子殼粉、纖維素粉末或其他固態載劑。 大itr混合物於現成可用之產品中之濃度可在相當 又化。通¥,調配物包含001至95重量%根據本發 明混合物,以〇.5至9〇重量0/〇較佳。 Λ 幻刀Α)與Β)與若需要時使用之c)可共同調配,但亦可分 周配及/或共同或分開施用至植物、其環境與/或種子 。最好同時施用活性成分。然而,亦可分開施用。 八同樣地,成份B)之兩種除葬劑可分開調配,及/或共同或 7刀開施用至植物、其環境與/或種子上。 此外,根據本發明除葬組合物與協同除莠混合物宜共同 與其他作物保護劑施用,例如:使用可控制植物病 原性真菌或細菌之農藥或藥劑。亦應注意其與礦物鹽溶液 <互洛性,後者係用於處理營養與微量元素缺乏症。亦可 添加無植物毒性之油類與油濃縮物。 虞本毛月/m 口物及除筹組合物可於植物萌發前或萌發 後施用。若有些作物較無法耐受活性成分時,所採用之施 :技術可藉喷灑設備之助’噴灑转組合物,因此儘可能 減少接觸敏感作物之葉部’同時使活性化合物到達該等作 :下面不要之植物葉部或未覆蓋之土壤表面(後置式(p〇st_ directed,lay-by))。 ^於萌發後處理植物時’根據本發明除荐组合物最好採 用茱邵施用法。施用法可例如:利用-般喷遲技術,使用 86907 -43- 200410634 水作為載劑,依約100至1000升/公頃之噴灑率噴灑混合物。 亦可能採用所謂之’’低體積法”與π超低體積法’,施用除莠組 合物,或以所謂之粒劑形式施用。 通常,協同除莠混合物中之A)、Β)與若需要時使用之c) 之含量重量比可產生協同效應。 混合物中之成分Α)與Β)之比例最好在1:〇.〇〇1至1:5〇〇之範 圍内,以1:0.01至1:100較佳,以1:0.1至1:50特別佳。 混合物中之成分Α)與C)之比例最好在1:〇·〇〇2至1:800之範 圍内,以1:0.003至1:250較佳,尤指1:0.003至1:160,以1:〇·〇2至 1:250特別佳,以1:0.02至1:160極特別佳。 純協同除荐混合物(亦即不含調配辅劑)之施用率為〇.2至 5000克/公頃活性物質(a.s.),尤指1至2000克/公頃,較佳為2 至2000克/公頃,特定言之8至1500克/公頃,依所計畫之目 的、季節、植物目標及生長階段而定。 式I 3-雜環基-取代之苯甲酸基衍生物之施用率為〇.ι至250 克/公頃活性物質(a.s·),通常為0.5至250克/公頃,尤指5至 250克/公頃,較佳為1〇至150克/公頃。 成分B)之較佳施用率為(^至?%克/公頃活性物質(as),通 常為〇·5至120克/公頃,尤指1至12〇克/公頃,較佳為10至1〇〇 克/公頃。 可視需要選用之成分C)之活性成分較佳施用率综合說明 於表2中。 表2 成分C 活性成分分類 活性成分 施用率 (克/公頃) 86907 -44 - 200410634 ci乙醯基CoA羧 抑制劑 s------ '---- ~~-- ~~^ 25-400 100-400 ------- 赛克定(cycloxydim) 100-400 — 希特定(sethoxydim) 100-400 三克定(tralkoxydim) 100-400 ---- 苯氧苯氧丙酸類 25-300 —--- 块丙基克丁弗-Pa (clodinafpop-P-propargyl)a 25-100 ——-_ 乙基分譜普 (fenoxaprop-ethyl) 50-300 乙基-P_芬諾普 (fenoxaprop-P-ethyl) 25-150 o乙醯基乳酸酯 合成酶抑制劑 0.2-800 ----- 咪嗤p林酮類 0.2-800 依滅草(imazapyr) 0.3-400 依滅克(imazaquin) 0.5-300 _____ 依滅本(imazamethabenz) 1-800 _____ 依滅比(imazapic) 0.2-400 ------------ 依滅特(imazethapyr) 0.3-150 ---~~~— 依滅莫(imazamox) 0.2-120 --—— π密淀基類 2-120 外I:硫貝酸鋼 (pyrithiobac-sodium) 2-120 ------ 磺醯胺類 1-225 ——~~·_- _ 伏速、爛(florasulam) 1-20 滅速爛(flumetsulam) 25-225 特速爛(metosulam) 1-60 1----- 磺醯脲類 1-120 —---- 甲基贺速能 (halosulfuron-methyl) 5-120 ------- 尼速能(nicosulfUron) 1-120 甲基普速能 (primisulfuron-methyl) 10-120 L——-__ 普洛速能(prosulfliron) 10-120 86907 -45 - 200410634 靈速能(rimsulfuron) 5-120 甲基地芬速能 (thifensulfuron-methyl) 10-60 甲基三本能 (tribenuron-methyl) 10-60 N_[[[4-甲氧基各(三氟甲 基)-1,3,5-三畊-2-基]胺 基]-羰基]-2-(三氟甲基)- 苯續醯胺 5-120 續速能(sulfosulfuron) 10-60 C3醯胺類 250-2000 - 伏賽滅(fluthiamide) 250-2000 C4植物生長素除 莠劑 25-750 吡啶羧酸類 25-750 陶斯松(clopyralid) 25-750 - 2,4-D 50-750 C5植物生長素運 輸抑制劑 15-100 - 大芬比(diflufenzopyr) 15-100 C6類胡蘿蔔素生 合成抑制劑 25-600 - 艾弗特(isoxaflutole) 25-200 - 速克酉同(sulcotrione) 100-600 - 滅奇酉同(mesotrione) 25-300 - 艾氯特(isoxachlortole) 25-200 - 奇特斯(ketospiradox) 25 -300 C7烯醇丙酮基莽 草酸-3-磷酸酯 合成酶抑制劑 (EPSPS) 360-1080 草甘膦(glyphosate) 360-1080 弗賽(sulfosate) 360-1080 C8麩醯胺合成酶 抑制劑 10-600 古弗辛銨 (glufosinate-ammonium) 10-600 86907 -46- 200410634 C9脂質生合成抑 制劑 ---- 60-4000 替苯胺類 60-4000 — ---—_ 大滅醯胺 (dimethenamid) 60-2000 — S-大滅醯胺 60-2000 '—---- '-------- ~ ----- 乙酉盈拉草(acetochlor) 滅多草(metolachlor) 250-4000 60-4000 硫服類 " S-滅多草 60-4000 100-4000 CIO有絲***抑制劑 --~~---~-__ 殺丹(benthiocarb) 1000- 4000 二硝基苯胺類 / V-/ V/ V-/ 375-3000 施得圃(pendimethalin) 375-3000 C11原卟啉原IX氧 化酶抑制劑 0.5-600 二苯基陡類 50-300 亞喜芬(acifluorfen) 50-300 亞喜芬鋼_ 50-300 吟二峻類 50-600 樂得奇(oxadiargy I) 50-600 環狀亞胺類 0.5-300 乙基卡芬松 (carfentrazone-ethyl) 0.5-35 乙基辛尼頓 (cinidon-ethyl) 3-35 戊基弗克拉 (flumiclorac-pentyl) 3-35 布塔芬(butafenacil) 5-300 JV485 50-300 C12光合作用抑制齋ί 15-4000 - 必汰草(pyridate) 250-1500 必達伏(pyridafol) 250-1000 苯並噻二畊酮類 30-1440 本達隆(bentazone) 30-1440 二伸被淀類 100-800 -47- 86907 200410634 巴拉刈二氯化物 (paraquat-dichloride) 100-800 脲類 250-1600 達有龍(diuron) 250-1600 異普特能(isoproturon) 250-1600 苯酚類 100-700 溴尼(bromoxynil) 100-700 克達松 (chloridazon) 500-4000 三畊類 15-4000 草脫淨(atrazine) 15-4000 脫別淨(terbutylazine) 250-4000 三畊酮類 30-300 滅必、淨(metribuzin) 30-300 C13協同製劑 500-1500 壤氧乙挺*類 500-1500 三地芬(tridiphane) 500-1500 C14生長物質 25-1200 芳氧烷酸類 50-1200 氟氯比(fluoroxypyr) 50-400 MCPA 400-1200 滅克普-P (mecoprop-P) 400-1200 苯甲酸類 75-800 汰克草(dicamba) 75-800 喹啉羧酸類 25-600 快克拉(quinclorac) 25-600 C16多種其他除莠劑 - 三亞凡(triaziflam) 50-750 &若適當時,亦可添加10-50克/公頃克昆赛(cloquintocet)。 【實施方式】 應用實例 根據本發明混合物係於萌發前與/或萌發後施用(葉部處 理)。成分B),及若需要時使用之成分C)之除莠化合物係以 市售產品之形式形成調配物施用。 86907 -48 - 200410634 成分A)、B),及若需要時使用之C)之除莠活性化合物係 連續或同時施用,後者係呈大槽混合物,有時候呈現成混 合物、乳液、水性溶液或懸浮液使用,其媒劑為水(300-400 升/公頃)。若進行田間試驗時,可藉助於移動式區間喷灑 器施用。 試驗期為3-8週。此期間後期亦觀察植株。 相較於未處理之對照組區間植物,採用0至100%之等級, 評估除莠組合物所造成之傷害。〇表示沒有損傷,100表示 植物完全損毁。 下列實例證實根據本發明使用之除莠組合物之作用,但 不排除其他用途之可能性。 此等實例中,若個別化合物之活性僅為加成性時,則採 用柯比(S· R· Colby)(1967)述於 ’’Calculating synergistic and antagonistic responses of herbicide combinations' Weeds 15,22 pp之方法計算期 望之E值。 採用下列公式 XY Too" E 二 X+ Y- 其中 X= X在施用率X時之除莠作用% ; Y= Y在施用率y時之除莠作用% ; E=成分X + Y在施用率x + y時之除莠作用期望值% ; 或採用下列公式 + XYZ 10000 E= X+ Y+ Z- (XY+ XZ+ YZ) 100 其中 86907 -49- 200410634 X= X在施用率X時之除莠作用%, Y= Y在施用率y時之除莠作用%, Z= Z在施用率z時之除莠作用%, 成分X+Y+ Z在施用率x+y + z時之除莠作用期望值%。 若所觀察到之數值高於依據柯比公式計算之E值時,則 具有協同效果。 根據本發明除莠混合物之除莠作用高於個別成分單獨使 用時依據柯比公式所計算得到之結果。 試驗結果示於下表3至17。 此等試驗中使用下列植物: 學名 俗名 Abutilon theophrasti 冏麻 Amaranthus retroflexus 藜 Avena fatua 野燕麥 Brachiaria plantaginea 亞歷山大草 Commelina benghalensis 熱帶鴨拓草 Echinochloa crus-galli 稗子 Galium aparine 豬決歹央 Pharbitis purpurea 牵牛花 Polygonum persicaria 春蓼 表3 :化合物Ia.29與依滅草(imazapyr)與依滅特(imazethapyr)1之 除莠作用(萌發後處理;溫室) 施用率(克/公頃 活性成分) 冏麻 柯比值E 受損[%] Ia.29 0.98 30 画 86907 -50- 200410634 依滅草(imazapyr) + 依滅特(imazethapyr) 0.98 20 - Ia.29 + 依滅草(imazapyr) 0.98 + 55 44 + 依滅特(imazethapyr) 0.98 表4 :化合物Ia.29與依滅草(imazapyr)與依滅特(imazethapyr)1之 除莠作用(萌發後處理;溫室) 施用率(克/公頃 熱帶鴨拓草 柯比值E 活性成分) 受損[%] Ia.29 3.91 50 - 依滅草(imazapyr) + 依滅特(imazethapyr) 3.91 10 - Ia.29 3.91 丁 依滅草(imazapyr) + 依滅特(imazethapyr) + 3.91 70 55 表5 :化合物Ia.29與依滅比(imazapic)與依滅草(imazapyr)2之除 莠作用(萌 發後處理 ;溫室) 施用率 (克/公頃 活性成分) 野燕麥 柯比值 藜 柯比值 受損[%] E 受損[%] E Ia.29 0.98 0 - 60 - 依滅比(imazapic) + 依滅草(imazapyr) 0.98 10 - 20 - Ia.29 0.98 | 卞 依滅比(imazapic) + 依滅草(imazapyr) + 0.98 40 10 75 68 86907 -51 - 200410634 表6 :化合物Ia.29與依滅比(imazapic)與依滅草(imazapyr)2之除 莠作用(萌發後處理;溫室) 施用率(克/公頃 野燕麥 柯比值E 活性成分) 受損[%] Ia.29 1.95 10 - 依滅比(imazapic) + 依滅草(imazapyr) 1.95 25 - Ia.29 1 1.95 | 十 依滅比(imazapic) + 依滅草(imazapyr) 十 1.95 60 33 表7 :化合物Ia.29與依滅草(imazapyr)與依滅特(imazethapyr)1與 草脫淨(atrazine)之除莠作用(萌發後處理;溫室) 施用率 (克/公頃活 性成分) 藜 柯比 值E 豬殃殃 柯比 值E 受損[%] 受損[°/〇] Ia.29 0.98 60 圆 20 - 依滅草(imazapyr) + 0.98 20 - 20 - 依滅特(imazethapyr) 草脫淨(atrazine) 15.6 40 - 0 - Ia.29 + 0.98 依滅草(imazapyr) + + 0.98 85 81 50 36 依滅特(imazethapyr) 4- + 卞 草脫淨(atrazine) 15.6 表8 :化合物Ia.29與依滅草(imazapyr)、依滅特(imazethapyr)1與 草脫淨(atrazine)之除莠作用(萌發後處理;溫室) 86907 -52- 200410634 施用率 豬殃殃 柯比值E (克/公頃活性成分) 受損[%] Ia.29 1.95 30 -、 依滅草(imazapyr) + 1.95 40 依滅特(imazethapyr) 草脫淨(atrazine) 31.25 20 - Ia.29 1.95 + + 依滅草(imazapyr) + 1.95 70 66 依滅特(imazethapyr) + + 草脫淨(atrazine) 31.25 表9 :化合物Ia.29與依滅比(imazapic)與依滅草(imazapyr)2與草 脫淨(atrazine)之除莠作用(萌發後處理;溫室) 施用率 (克/公頃活性成分) 冏麻 柯比值E 受損[%] Ia.29 7.81 85 - 依滅比(imazapic) + 7.81 70 - 依滅草(imazapyr) 草脫淨(atrazine) 125 30 - Ia.29 + 7.81 依滅比(imazapic) + + 7.81 100 97 依滅草(imazapyr) + + 草脫淨(atrazine) 125 86907 -53 - 200410634 表10 :化合物Ia.29與依滅草(imazapyr)與依滅特(imazethapyr)1與 草脫淨(atrazine)之除莠作用(萌發後處理;溫室) 施用率 (克/公頃活 亞歷山 大草 柯比 值E 稗子 柯比 值E 性成分) 受損[%] 受損[%] Ia.29 + 7.81 依滅草(imazapyr) + 85 - 80 - 卞 依滅特(imazethapyr) 7.81 草脫淨(Atrazine) 125 25 - 30 Ia.29 4- 7.81 I 依滅草(imazapyr) + 依滅特(imazethapyr) + 7.81 4- 100 89 100 86 \ 草脫淨(atrazine) 1 125 表11 :化合物Ia.29與依滅草(imazapyr)與依滅特(imazethapyr)1與 草脫淨(atrazine)之除莠作用(萌發後處理;溫室) 施用率 (克/公頃活 性成分) 豬歹央歹央 柯比 春蓼 柯比 受損[%] 值E 受損[%] 值E Ia.29 + 7.81 依滅草(imazapyr) 4- + 70 - 75 - 卞 依滅特(imazethapyr) 7.81 草脫淨(atrazine) 125 60 - 60 Ia.29 4- 7.81 依滅草(imazapyr) + + 7.81 98 88 100 90 依滅特(imazethapyr) 4- + 卞 草脫淨(atrazine) 1 125 86907 -54- 200410634 表l2 ··化合物Ia.:29、依滅草(imazapyr)與依滅特(imazethapyr)1與 草脫淨(atrazine)之除莠作用(萌發後處理;溫室) 施用率 (克/公頃活 性成分) 稗子 柯比 牽牛花 柯比 受損[%] 值Ε 受損[%] 值Ε Ia.29 + 依滅草(imazapyr) 4- 3.91 + 85 50 十 依滅特(imazethapyr) 3.91 草脫淨(atrazine) 62.5 20 - 80 Ia.29 + 3.91 依滅草(imazapyr) + 依滅特(imazethapyr) 4- + 3.91 -μ 95 88 100 90 卞 草脫淨(atrazine) 62.5 表13 :化合物Ia.29、依滅草(imazapyr)與依滅特(imazethapyr)1與 __草脫淨(atrazine)之除莠作用(萌發後處理;溫室) 施用率 春蓼 柯比值E (克/公頃活性成分) 受損[%] Ia.29 + 3.91 依滅草(imazapyr) + 依滅特(imazethapyr) + 3.91 70 - 草脫淨(atrazine) 62.5 40 - Ia.29 + 3.91 依滅草(imazapyr) + + 3.91 100 82 依滅特(imazethapyr) 4- 卞 草脫淨(atrazine) 丁 62.5 86907 -55- 200410634 表14 :化合物Ia.29、依滅比(imazapic)與依滅草(imazapyr)2與草 _脫淨(atrazine)之除莠作用(萌發後處理;溫室) 施用率 (克/公頃活 性成分) 稗子 柯比 商麻 柯比 受損[%] 值E 受損[%] 值E Ia.29 + 7.81 依滅比(imazapic) + 80 - 85 - 依滅草(imazapyr) 7.81 草脫淨(atrazine) 125 30 - 30 Ia.29 + 7.81 依滅比(imazapic) + + 7.81 100 86 100 90 依滅草(imazapyr) 4- 1 草脫淨(atrazine) 1 125 表15 :化合物Ia.29、依滅比(imazapic)與依滅草(imazapyr)2與草 脫淨(atrazine)之除莠作用(萌發後處理;溫室) 施用率 豬殃殃 柯比值E (克/公頃活性成分) 受損[%] Ia.29 + 7.81 依滅比(imazapic) + 80 - 卞 依滅草(imazapyr) 7.81 草脫淨(atrazine) 125 60 Ia.29 + 7.81 1 依滅比(imazapic) + + 7.81 98 92 依滅草(imazapyr) + + 草脫淨(atrazine) 125 86907 -56- 200410634 表16 :彳匕合物Ia.29、依滅比(imazapic)與依滅草(imazapyr)2與草 _ 脫淨(atrazine)之除莠作用(萌發後處理;溫室) 施用率 (克/公頃活 性成分) 亞歷山 大草 柯比 值E 裨子 柯比 值E 受損[%] 受損[%] Ia.29 + 依滅比(imazapic) + 依滅草(imazapyr) 3.91 + 3.91 85 - 80 - 草脫淨(atrazine) 62.5 20 - 20 Ia.29 + 依滅比(imazapic) + 依滅草(imazapyr) + 草脫淨(atrazine) 3.91 + 3.91 + 62.5 100 88 98 84 表17 ··化合物Ia.29、依滅比(imazapic)與依滅草(imazapyr)2與草 脫淨(atrazine)之除莠作用(萌發後處理;溫室) 施用率 春蓼 柯比值E (克/公頃活性成分) 受損[%] Ia.29 + 依滅比(imazapic) 4- 3.91 + 70 麵 卞 依滅草(imazapyr) 3.91 草脫淨(atrazine) 62.5 40 - Ia.29 + 3.91 1 依滅比(imazapic) + 依滅草(imazapyr) _L + 3.91 + 100 82 卞 草脫淨(atrazine) 1 62.5 86907 -57- 200410634 1 依滅草(imazapyr):依滅特(imazethapyr) = 1:3 2依滅比(imazapic):依滅草(imazapyr)=3:1 86907 58-R1 is _ prime or CrC6-alkyl; and 圮 is 4,5_ monohydroiso-5-wa-3-yl which may be substituted one or more times without substitution or by the following groups: _ prime, CVC4, alkyl, CrCr alkoxy 86907 -31- 200410634, CpCrii alkyl, CrCpii alkoxy or CrC4-alkylthio; R3 is Ci-C6-continuous test group, and R4 is hydrogen. The most particularly preferred is 4- [2-chloro · 3- (4,5-dihydroisopurazol-3-yl) -4-methylsulfonyl-benzyl] -1-methyl-5-hydroxy -1H-pyrazole. Most preferred is also 4- [2-methyl-3- (4,5-dihydroisoxazol-3-yl) -4-methylsulfonyl-benzyl] -1-methyl-5 -Hydroxy-1H-pyrazole. A preferred aspect of the synergistic herbicidal effect of the mixture according to the present invention is that they include a mixture of imazapyr and imazethapyr, or imazapyr and imazapic as component B) , Especially a mixture containing imazapyr and imazethapyr as component B). In another preferred aspect, the synergistic herbicidal mixture comprises three herbicidal active compounds: a compound of formula I (ingredient A) and two herbicides selected from the group consisting of: imazapyr, Imazaquin, imazamethabenz-methyl, imazamox, imazapic and imazethapyr (ingredient B). -In the particularly preferred embodiments, the above-mentioned preferred embodiments are also applicable. In particular, the synergistic herbicide mixture contains 4- [2-methyl-3- (4,5-dihydroisoxazol-3-yl) -4-methylsulfonyl-benzyl group as component A ] -1-Methyl-5-acyl-lH-ρ bijun and two herbicides selected from the group consisting of imazapyr, imazaquin, methyl Ezaben (imazamethabenz-methyl), imazamox, imazapic and imazethapyr (ingredient B). 86907 -32- 200410634 A particularly preferred synergistic herbicide mixture contains 4- [2-methyl-3--(4,5-dihydroisoxazol-3-yl) -4-methanesulfonyl- as component A- Benzamidine] -1-methyl-5-meryl-1Η-ρ bitol and imazapyr and imazethapyr as component B). In another specific embodiment, synergy The herbicide mixture contains 4- [2-methyl- 3- (4,5-dimuridine 1: 7-ortho-3-yl) -4-methylphenoxy-benzylidene] as component A] 1-methyl-5-hydroxy-1H-pyrazole and imazapyr and imazapic as component B). In another preferred embodiment, the synergistic herbicidal mixture comprises at least four herbicidal active compounds: a compound of formula I (ingredient A), two herbicidal agents selected from the group consisting of: Grass (imazapyr), imazaquin, imazamethabenz-methyl, imazamox, imazapic and imazethapyr (ingredients B and C) At least one herbicide compound selected from the group consisting of acetamyl CoA carboxylase inhibitor (ACC), acetamyl lactate synthase inhibitor (ALS), amidines, auxin herbicides, plant growth Transport inhibitors, carotenoid biosynthesis inhibitors, enolacetone shikimate 3-phosphate synthase inhibitors (EPSPS), glutamine synthetase inhibitors, lipid biosynthesis inhibitors, mitotic inhibitors, Proto-W, p-Prime IX oxidase inhibitors, photosynthesis inhibitors, synergistic agents, growth substances, inhibitors of cell wall biosynthesis, and various other herbicides. From the viewpoint of the synergistic elimination effect of the mixture comprising the components A), B) and C) according to the present invention, it is preferred to use a compound selected from the group C1 to C14 or C16 as the component C), preferably from C9 and C12 ethnic group. 86907 -33- 200410634 In particular, compounds selected from the active ingredient types described below are preferred, or the following compounds are particularly preferred: C1 Acetyl CoA carboxylase inhibitor (ACC):- Cyclohexenone M acids, specifically: cycloxydim, sethoxydim, or tralkoxydim, preferably sethoxydim or tralkoxydim; or -benzene Oxyphenoxypropionates, specifically: clodinafop-propargyl (and cloquintocet if appropriate) Φ, fenoxaprop-ethyl or P -Ethylfenoxol, preferably clodinafop-propargyl (and cloquintocet if appropriate) or P-ethylfenoxol; C2 ethynyl lactate Synthetase inhibitors (ALS):-michelin, specifically: imazapyr, imazaquin, imazamethabenz, imazethapyr, or imazamo (Imazamox), preferably imazapyr; -pyrimidyl ethers, in particular ... pyrithi obac sodium);-Continue brewing amines, specifically: florasulam, flumetsulam or metosulam, preferably metosulam; or-Continue S Sheng Basic ureas, specifically: halosulfliron-methyl, nicosulfUron, primisulfuron methyl, prosulfUron, rimsulfhron ), Thifensulforon-methyl, methyltristin 86907 -34-200410634 (tribenuron-methyl), N-[[[4-methoxy-6- (trifluoromethyl) -l, 3,5-Tricotyl-2-yl] -amino] carbonyl] -2- (trifluoromethyl) -benzenesulfonamide or sulfosulfuron; C3 sulfonamides: -fluthiamide ); C4 auxin herbicides:-pyridine carboxylic acids, in particular: closyralid; or -2,4-D; C5 auxin transport inhibitors:-diflufenzopyr; C6 Carotenoid synthesis inhibitor:-isoxaflutole, mesotrione, isoxachloride, ketospiradox or sulcotrione (chlormesulone) , In particular, isoxaflutole or sulcotrione; C7 enol acetoxyshikimate-3-phosphate synthase inhibitor (EPSPS): -glyphosate or forsythia ( sulfosate); C8 glutamine synthetase inhibitors: _ glufosinate-ammonium; C9 lipid biosynthesis inhibitors:-chloroacetamidine, specifically: dimethenamid, S -Acetaminophen, acetochlor, metolachlor or S-metachlor;-thioureas, specifically: benthiocarb; 86907 -35- C10 mitotic inhibition Agents: nitroanilines, specifically · Shidipu (pendimethalin); C11 protoporphyrinogen〗 Sense oxidase inhibitors: • -phenyl ethers, specifically: acifluorfen or sub Xifen sodium;-'disials, specifically: oxadiargyl; or-cyclic imines, specifically: butafenacil, carfentrazone-ethyl, Ethyl Cindon-Ethyl or Flumiclorac-Pentyl, preferably Ethyl Carfensone (Carfentrazone-ethyl), cinidon-ethyl or flumidorac-pentyl; -pyrazoles, specifically JV 85; C12 photosynthesis inhibitors: -pyridate ) Or pyridafol, specifically pyridate; -benzo p-cetophenones, specifically benzone (bentazone); -di-exponiolides, specifically: Paraquat-dichloride;-ureas, specifically: diuron or isoproturon, preferably diuron;-benzene test, Specific words: bromoxynil;-chloridazone;-trisomies, specific words atrazine or terbutylazine; or 86907 -36- 200410634-triple p wells Ketones, specifically: metribuzin; C13 synergistic preparations: -Ethylene oxide, specifically: tridiphane; C14 growth substances: -Aryloxy acids, specifically: Fluoroxypyr, MCPA or mecoprop-P;-benzoic acids, specifically: dicamba; or-quinic acid, Given words: Fast carat (quinclorac); C16 various other herbicides: - Where Sanya (triaziflam). In particular, compounds selected from the active ingredient categories described below are preferred, or the following compounds are particularly preferred: C9 Lipid Biosynthesis Inhibitor: -Acetoline aniline, specifically: fenamic acid (dimethenamid), S-dimethenamid, acetochlor, metolachlor, or S-metachlor; C12 photosynthesis inhibitor: -pyridate; benzopyrene Ketones, specifically: Bentazone;-Bisymmetry, specifically: Paraquat-dichloride;-Ureas, specifically: Dayoulong (Diuron) or isoproturon, preferably diuron;-benzene age, specifically: bromoxynil; 86907 -37- 200410634-chloridazon (chloridazon); -Three farming species, specifically: atrazine or terbutylazine; or-three p well ketones, specifically: metribuzin. In a particularly preferred embodiment, the above The preferred embodiments are equally applicable. A particularly preferred synergistic dephosphorization mixture contains 4- [2-methyl-3- (4,5-dihydroisozazol-3-yl) -4-methylsulfonyl-benzyl] as component A- 1-methyl-5-hydroxy · 1H-pyrazole; as ingredient B, two herbicides selected from the group consisting of imazapyr, imazaquin, and formazan Imazamethabenz-methyl, imazamox, imazapic, and imazethapyr; and an herbicide compound selected from the C9 group as component C, specifically Chlorhexidine, especially acetochlor. A particularly preferred synergistic herbicide mixture contains 4- [2-methyl-3- (4,5-diazaisoptopyryl-3-yl) -4-formamic acid-benzoic acid group] as component A- 1-methyl-5-lightyl-1H-Eη sits; imazapyr and imazethapyr as ingredients B, and chloroethoxybenzidine as the ingredient C, especially ass Pull grass (acetochlor). A particularly preferred synergistic herbicide-killing mixture contains 4- [2-methyl-3- (4,5-dihydroisoisothione-3-yl) -4-methyloxanyl-benzylidene] as component A] -1-methyl_5_lightyl-1H-pyrazole; imazapyr and imazapic as component B; and chloroacetamidine aniline as component C, especially ethirab Grass (acet〇chlr). Also particularly preferred is a synergistic herbicide mixture which contains 4- [2-methyl-3- (4,5-dihydroiso4-tetra-3-yl) -4-formyl-benzyl] as component A] Methylalyl-1H-pyrazole, two ingredients as component B selected from the group consisting of 86907 -38- 200410634 tincture: imazapyr, imazaquin, a Imazamethabenz-methyl, imazamox, imazapic, and imazethapyr; and a compound C selected from the group C12, among other compounds, specifically three P-wells, especially atrazine or benzo-p-diketone, especially bentazone. A particularly good synergistic herbicidal mixture contains 4- [2-methyl-3- (4,5-dirhamisoiso-4-oxo-3-yl) -4-methyloxoyl-benzyl] as component A] -1-methyl-5-stilbyl-lHw specific bite; imazapyr and imazethapyr as ingredient B, and three p-wells as ingredient C, especially grass removal ( atrazine). A particularly preferred synergistic herbicide mixture contains 4- [2-methyl-3- (4,5-dihydroisopurinazol-3-yl) -4-methylsulfonyl-benzyl] as component A- 1-fluorenyl-5-hydroxy-1Η-ρ-bito; imazapyr and imazethapyr as component B, and benzo-p-di-pione ketones as component C, especially Refers to bentazone. A particularly preferred synergistic desulfurization mixture contains 4- [2-methyl-3- (4,5-dihydroisohumazol-3-yl) -4-fluorenylsulfonyl-benzyl] as component A- 1-methyl-5-hydroxy-1H-mouth-to-mouth sitting; as ingredients B, imazapyr and imazapic; and as a component of Cultivation, especially grass ). A particularly good synergistic herbicidal mixture contains 4- [2-methyl-3- (4,5-diazepine 17--3-yl) -4-methyl-6-benzyl-benzoate] as component A] -1-methyl-5- mesityl-lH-ρ-bito; imazapyr and imazapic as component B; and benzo-p-diphenylpyridine as component C, Especially bentazone. The invention also extends to a scavenger composition comprising a synergistic scavenger mixture (containing ingredients A), B) as described above and C)) if required, at least one liquid and / or Solid carrier and, if required, at least one surfactant, 86907-39-200410634. The herbicidal composition and synergistic herbicidal mixture according to the present invention have excellent control effects on broad-leaved weeds and herbaceous weeds in crops (such as corn, cereals, rice, and soybeans), but will not harm crop plants, especially in This effect is still visible at very low application rates. According to the present invention, the herbicidal composition and the synergistic herbicidal mixture can be used in consideration of a variety of different application methods and also applied to other various crop plants to eliminate unwanted plants. Examples of suitable crops are: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Steamed vegetables (Beta vulgaria ssp · altissima, Beta vulgaria ssp · rapa), Brassica napus var · napus, Brasaica napus var · napobrassica, Brassica rapa var · silvestris), camellia (Camellia sinensis), I flower (Carthamus tinctorius), Carya illinoinensis, Citrus limon, hanging orange ( Citrus sinensis), Coffee (Coffea canephora, Coffeea liberica), Cucumis sativus, Cynodon dactylon, Carrot (Daucus carota), Elaeis guineensis, Fragaria vesca, Soybean (Glycine max), cotton (Gossypium hirsuUim) (Gossypium arboreum 'Gossypiumherbaceum ^ Gossypium vitifolium), Helianthua annuus, Hevea brasiliensis, Hordeum vulgareum, beer Ipomoea batatas), Juglans regia, Lens culi naris), flax (Linum usitatissimum), Fanchi (Lycopersicon lycopersicum), apple (Malus spp.), white aconite (Manihot esculenta), alfalfa (Medicago sativa), plantain (Musa spp ·), nicotiana tabacum (Nicotiana tabacum) ( N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, cloud 86907 -40- 200410634 Picea abies, Pinus spp., Bowl bean ( Pisum sativum), Plum (Pmnus — avium), Primus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale ,% (Solanum tuberosum), Sorghum bicolor (S.vulgare), cocoa; f seal (Theobroma cacao), clover (Trifolium pratense), wheat (Triticum aestivum), durum (Triticum durum), broad bean (Vicia faba), grapes (Vitis vinifera) and corn (Zea mays). In addition, the herbicide composition and the synergistic herbicide mixture according to the present invention can also be used in crops that are resistant to herbicide effects due to breeding (including genetic engineering). The mixture or the herbicidal composition containing the same according to the present invention may be, for example, an aqueous solution, powder, suspension, and high-concentration aqueous, oily or other suspension or homogeneous solution, emulsion, oil homogeneous solution that can be sprayed directly. , Paste, fine powder, spreading material or granules, etc., by spraying, aerosolizing, dusting, spreading or pouring. The use pattern depends on the intended purpose; in any case, it should be ensured that the active ingredient according to the invention can be distributed uniformly. Appropriate inert adjuvants are medium-boiling to high-boiling mineral oil fractions, such as: kerosene and diesel, and coal tar and vegetable or animal oils, and aliphatic, ring and aromatic hydrocarbons, such as paraffin, tetrahydrofuran, Alkylated fluorene and its derivatives, alkylated benzene and its derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strong polar solvents such as: N-methyl orbitolone and water. Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules with water. Preparation of emulsion, paste or oil homogeneous 86907 -41-200410634 :: 时 'After the substance is itself or dissolved in oil or solvent, the water is used to homogenize the use of :: agent' adhesive, dispersant or emulsifier. However, it can also be used to make sex substances, wetting agents, adhesives, powders or emulsifiers, and if = concentrates consisting of solvents or oils, suitable surfactants for these concentrates are: metal test, Aromatic hand of aging soil golden wheel =: two examples: lignin continued acid salt, phenylsulfonium salt, sulfonium salt and mono- " butyl-qinite phyllate, in L, burn A to dissociate-and Lufang -Continuous acid salt, soil L h, lauryl ether sulfate, cetyl alcohol 'heptadecyl alcohol and stearyl alcohol =% sulfate, and sulfuric acid tea and its derivatives with Jia Junzhi, • Condensation products, condensed products of naphthalenes, benzene, and Jiajun "Ge, ethoxylated isooctyl age, ethoxy, t-octyl phenyl ether polyphenylene ether, 4 or ethoxylated nonyl fluorene , Alkanes, Isotridecyl Alcohol, Moon Ice II_, Burning Polyaryl Alcohol Oil, Polyoxyethylene Alkyl Diol, Ethoxymethylene Glycol Ether Acetate, Mountain Thorny, Cloth I-based ethers, lauryl alcohol-based cellulose. Mubein sulphite waste liquid or nail preparation powder for 'removal of materials', * ,, or individual active ingredients can be used for training when it is trained. Preparation of granules with synergistic elixirs mixture, such as :: m. Grinding. The active ingredient and solid can be loaded with 2, while the anti-foaming granules and homogeneous granules, the stone, silicone, silicate, and solid solid carrier can be Mineral soils such as silicon, block clay, loess, clay back, soil, limestone, lime, chalk dolomite, diatomaceous earth, calcium sulfate, sulfur 86907 -42-: magnesium oxide, synthetic grinding powder, fertilizer such as: sulfuric acid Ammonium, ammonium phosphate, glutenin, and plant-based products such as: cereal flour, bark flour, wood flour, shell powder, cellulose powder, or other solid carriers. The concentration of the large itr mixture in ready-to-use products can be In the equivalent, the formulation contains 001 to 95% by weight of the mixture according to the invention, preferably 0.5 to 90% by weight 0 / 〇. Λ Magic Knife A) and B) and c if needed ) Can be formulated together, but can also be applied weekly and / or jointly or separately to plants, their environment and / or seeds. It is best to apply the active ingredients simultaneously. However, they can also be applied separately. Similarly, ingredients B) The two fungicides can be formulated separately and / or applied to the plant together or 7-knife Its environment and / or seeds. In addition, the fungicide composition and synergistic herbicide mixture according to the present invention should be applied together with other crop protection agents, for example, using pesticides or agents that can control phytopathogenic fungi or bacteria. It should also be noted Mineral salt solution < Interlude, the latter is used to treat nutrition and trace element deficiency. Non-phytotoxic oils and oil concentrates can also be added. Yuben Maoyue / m Mouthpiece and herb removing composition can be applied before or after germination of plants. If some crops are less able to tolerate the active ingredients, the application method: technology can be used to spray the transfer composition with the help of spray equipment, so as to minimize contact with the leaves of sensitive crops, while allowing the active compounds to reach the crop: Unwanted plant leaves or uncovered soil surfaces (post-directed, lay-by). ^ When plants are treated after germination ', the decommissioning composition according to the present invention is preferably applied by the method of cinnabar. The application method can be, for example, using a general spraying technique, using 86907 -43- 200410634 water as a carrier, and spraying the mixture at a spray rate of about 100 to 1000 liters / ha. It is also possible to use the so-called "low volume method" and the π ultra-low volume method, to apply the herbicide composition, or to apply it in the form of so-called granules. Generally, A), B) in the herbicide mixture are combined with The content weight ratio of c) used at the time can produce a synergistic effect. The ratio of the components A) and B) in the mixture is preferably in the range of 1: 0.01 to 1: 500, and from 1: 0.01 to 1: 100 is preferred, and 1: 0.1 to 1:50 is particularly preferred. The ratio of the components A) and C) in the mixture is preferably in the range of 1: 0.002 to 1: 800, and 1: 0.003. It is preferably from 1: 250, especially from 1: 0.003 to 1: 160, particularly preferably from 1: 0.002 to 1: 250, and particularly preferably from 1: 0.02 to 1: 160. Pure synergistic mixtures (also The application rate is 0.2 to 5000 g / ha of active substance (as), especially 1 to 2000 g / ha, preferably 2 to 2000 g / ha, specifically 8 to 1500. G / ha, depending on the planned purpose, season, plant target and growth stage. Formula I 3-heterocyclyl-substituted benzoic acid derivatives are applied at a rate of from 0.005 to 250 g / ha (As ·), usually 0.5 to 250 / Ha, especially 5 to 250 g / ha, preferably 10 to 150 g / ha. The preferred application rate of ingredient B) is (^ to?% G / ha active substance (as), usually 0 ·· 5 to 120 g / hectare, especially 1 to 120 g / hectare, preferably 10 to 100 g / hectare. The optional application rate of the active ingredient C) can be selected as required. Table 2 Ingredient C Classification of Active Ingredients Active Ingredient Application Rate (g / ha) 86907 -44-200410634 Ci Acetyl CoA Carboxy Inhibitors ------ '---- ~~-~~ ^ 25- 400 100-400 ------- cycloxydim 100-400-sethoxydim 100-400 trilkoxydim 100-400 ---- phenoxyphenoxypropionic acid 25- 300 ----- clodinafpop-P-propargyla 25-100 ----- fenoxaprop-ethyl 50-300 fenoxaprop-ethyl fenoxaprop-P-ethyl) 25-150 o Ethyl lactate synthase inhibitor 0.2-800 ----- imazapyrrin 0.2-800 imazapyr 0.3-400 imazaquin) 0.5-300 _____ imazamethabenz 1-800 _____ Imazapic 0.2-400 ------------ imazethapyr 0.3-150 --- ~~~-imazamox 0.2-120 ------ π Wyodo base class 2-120 Outer I: pyrithiobac-sodium 2-120 ------ sulfonamides 1-225 ---- ~~ · _- _ volt speed, rotten (florasulam) 1-20 flumetsulam 25-225 metosulam 1-60 1 ----- sulfonylureas 1-120 ------ methyl halosulfuron-methyl 5 -120 ------- Nicosulfuron 1-120 Primisulfuron-methyl 10-120 L -----__ Prosulfliron 10-120 86907 -45- 200410634 rimsulfuron 5-120 thifensulfuron-methyl 10-60 tribenuron-methyl 10-60 N _ [[[4-methoxymethoxy ((trifluoromethyl ) -1,3,5-Trigon-2-yl] amino] -carbonyl] -2- (trifluoromethyl) -benzodiazepine 5-120 sulfosulfuron 10-60 C3 amine Class 250-2000-fluthiamide 250-2000 C4 auxin herbicide 25-750 pyridinecarboxylic acid 25-750 clopyralid 25-750 -2,4-D 50-750 C5 auxin transport inhibitor 15-100-Diflufenzopyr 15-100 C6 carotenoid biosynthesis inhibitor 25-600-isoxaflutole 25-200 -Sulcotrione 100-600-mesotrione 25-300-isoxachlortole 25-200-ketospiradox 25 -300 C7 enolacetone shikimic acid-3 -Phosphate synthetase inhibitor (EPSPS) 360-1080 glyphosate 360-1080 sulfosate 360-1080 C8 glutamine synthetase inhibitor 10-600 glufosinate-ammonium 10-600 86907 -46- 200410634 C9 Lipid Biosynthesis Inhibitor ---- 60-4000 Diphenylamines 60-4000 — --- —_ Dimethenamid 60-2000 — S-Dimethamine 60-2000 '------' -------- ~ ----- acetochlor metolachlor 250-4000 60-4000 sulfur suits " S-metachlor Grass 60-4000 100-4000 CIO mitotic inhibitor-~~ --- ~ -__ benthiocarb 1000- 4000 dinitroaniline / V- / V / V- / 375-3000 Shidi Pu (pendimethal in) 375-3000 C11 protoporphyrinogen IX oxidase inhibitor 0.5-600 diphenyl steep 50-300 acifluorfen 50-300 Axifen steel _ 50-300 Yin Erjun 50-600 Oxadiargy I 50-600 cyclic imines 0.5-300 carfentrazone-ethyl 0.5-35 cinidon-ethyl 3-35 flumiclorac- pentyl) 3-35 butafenacil 5-300 JV485 50-300 C12 photosynthesis inhibition 15-4000-pyridate 250-1500 pyridafol 250-1000 benzothiazine Ketones 30-1440 Bentazone 30-1440 Two stretches 100-800 -47- 86907 200410634 Paraquat-dichloride 100-800 Urea 250-1600 diuron 250-1600 isoproturon 250-1600 phenol 100-700 bromoxynil 100-700 chloridazon 500-4000 atrazine 15-4000 atrazine 15 -4000 terbutylazine 250-4000 mesotrione 30-300 metribuzin 30-300 C13 synergistic preparation 500-1500 Ethoxylate * class 500-1500 tridiphane 500-1500 C14 growth substance 25-1200 aryloxyalkanoic acid 50-1200 fluoroxypyr 50-400 MCPA 400-1200 Mecoprop-P 400-1200 benzoic acid 75-800 dicamba 75-800 quinoline carboxylic acid 25-600 quinclorac 25-600 C16 various other herbicides- Triaziflam 50-750 & if appropriate, 10-50 g / ha cloquintocet can also be added. [Embodiment] Application examples The mixture according to the present invention is applied before germination and / or after germination (leaf treatment). The herbicidal compound of ingredient B), and ingredient C) used if necessary, is applied as a formulation in the form of a commercially available product. 86907 -48-200410634 Ingredients A), B), and if necessary C) the herbicidal active compounds are applied continuously or simultaneously, the latter being a large tank mixture, sometimes as a mixture, emulsion, aqueous solution or suspension For liquid use, the vehicle is water (300-400 l / ha). For field trials, it can be applied with the help of mobile interval sprayers. The trial period is 3-8 weeks. Plants were also observed later in this period. Compared with the untreated control interval plants, a scale of 0 to 100% was used to evaluate the damage caused by the herbicide composition. ○ means no damage, and 100 means complete plant damage. The following examples confirm the effect of the herbicidal composition used according to the present invention, but do not exclude the possibility of other uses. In these examples, if the activity of an individual compound is only additive, use S.R. Colby (1967) described in `` Calculating synergistic and antagonistic responses of herbicide combinations' Weeds 15, 22 pp. The method calculates the expected E value. The following formula is used: XY Too " E two X + Y- where X = X% of the herbicide at the application rate X; Y = Y% of the herbicide at the application rate y; E = ingredient X + Y at the application rate x + Expected value of herbicidal effect at y; or use the following formula + XYZ 10000 E = X + Y + Z- (XY + XZ + YZ) 100 where 86907 -49- 200410634 X = X's herbicidal effect at application rate X, Y =% Scavenger effect of Y at application rate y, Z =% scavenger effect of Z at application rate z, and expected value of scavenger effect of ingredient X + Y + Z at application rate x + y + z. If the observed value is higher than the E value calculated according to the Kirby formula, it has a synergistic effect. The thallium removal effect of the thallium removal mixture according to the present invention is higher than the result calculated according to the Kirby formula when the individual ingredients are used alone. The test results are shown in Tables 3 to 17 below. The following plants were used in these experiments: Scientific name Abutilon theophrasti Ramie Amaranthus retroflexus Quinoa Avena fatua Wild oat Brachiaria plantaginea Alexandra Commelina benghalensis Tropical Duckweed Echinochloa crus-galli Gardenia Galium aparine Pig Cleopatra Pharbitis puraria reaperium perum 3Table 3: Compound Ia.29's herbicidal action with imazapyr and imazethapyr1 (post-germination treatment; greenhouse) Application rate (g / ha active ingredient) Ramie ratio E impaired [%] Ia.29 0.98 30 Painting 86907 -50- 200410634 Imazapyr + imazethapyr 0.98 20-Ia.29 + imazapyr 0.98 + 55 44 + imazethapyr ) 0.98 Table 4: Compound Ia.29's herbicidal action with imazapyr and imazethapyr 1 (post-germination treatment; greenhouse) Application rate (g / ha Tropical duck Tuo Ke Ke value E Active ingredient ) Damage [%] Ia.29 3.91 50-Imazapyr + imazethapyr 3.91 10-Ia.29 3.91 Ding Yifen imazapyr) + imazethapyr + 3.91 70 55 Table 5: Extermination effect of compound Ia.29 and imazapic and imazapyr 2 (post-germination treatment; greenhouse) application rate (g Per hectare active ingredient) Wild oat keto ratio quinoa and keto ratio impaired [%] E impaired [%] E Ia.29 0.98 0-60-imazapic + imazapyr 0.98 10-20- Ia.29 0.98 | Imazapic + imazapyr + 0.98 40 10 75 68 86907 -51-200410634 Table 6: Compound Ia.29 and imazapic and imazapyr ) 2 (post-germination treatment; greenhouse) application rate (g / ha wild oat Kirby ratio E active ingredient) impaired [%] Ia.29 1.95 10-imazapic + imazapyr ) 1.95 25-Ia.29 1 1.95 | Imazapic + imazapyr 10.1.95 60 33 Table 7: Compounds Ia.29 and imazapyr and imazethapyr 1 The herbicidal effect of atrazine (post-germination treatment; greenhouse) Application rate (g / ha active ingredient) Chenopodium Value E Pork ratio E Damage [%] Damage [° / 〇] Ia.29 0.98 60 Round 20-imazapyr + 0.98 20-20-imazethapyr atrazine) 15.6 40-0-Ia.29 + 0.98 imazapyr + + 0.98 85 81 50 36 imazethapyr 4- + atrazine 15.6 Table 8: Compounds Ia.29 and Elimination of imazapyr, imazethapyr 1 and atrazine (post-germination treatment; greenhouse) 86907 -52- 200410634 Application rate Hog's ratio E (g / ha activity Ingredients) Damage [%] Ia.29 1.95 30-, imazapyr + 1.95 40 imazethapyr atrazine 31.25 20-Ia.29 1.95 + + imazapyr + 1.95 70 66 imazethapyr + + atrazine 31.25 Table 9: Compound Ia.29 divided by imazapic and imazapyr 2 and atrazine Tritium effect (post-germination treatment; greenhouse) Application rate (g / ha active ingredient) Impaired ramie ratio E [ %] Ia.29 7.81 85-imazapic + 7.81 70-imazapyr atrazine 125 30-Ia.29 + 7.81 imazapic + + 7.81 100 97 according to Imazapyr + + atrazine 125 86907 -53-200410634 Table 10: Compound Ia.29 and imazapyr and imazethapyr 1 and atrazine Tritium effect (post-germination treatment; greenhouse) Application rate (g / ha live Alexander grass Kobe E E Gardenia Kobe E Sexual component) Damage [%] Damage [%] Ia.29 + 7.81 imazapyr + 85-80-imazethapyr 7.81 Atrazine 125 25-30 Ia.29 4- 7.81 I imazapyr + imazethapyr + 7.81 4- 100 89 100 86 Atrazine 1 125 Table 11: Pyramidal effect of compound Ia.29 and imazapyr and imazethapyr 1 and atrazine (post-germination treatment; greenhouse) application Rate (g / ha active ingredient) Pork 歹 歹 歹 比 Kirby 蓼 蓼 Kirby is damaged [%] Value E Damaged [%] Value E Ia.29 + 7.81 imazapyr 4- + 70-75-imazethapyr 7.81 atrazine 125 60-60 Ia.29 4- 7.81 imazapyr + + 7.81 98 88 100 90 imazethapyr 4- + atrazine 1 125 86907 -54- 200410634 Table l2 ·· Compound Ia .: 29. (Imazapyr) and imazethapyr 1 and atrazine (post-germination treatment; greenhouse) Application rate (g / ha active ingredient) Gardenia Kirby Petunias Kirby damaged [%] Value E damaged [%] Value EA Ia.29 + imazapyr 4- 3.91 + 85 50 imazethapyr 3.91 atrazine 62.5 20-80 Ia.29 + 3.91 isoam Grass (imazapyr) + imazethapyr 4- + 3.91 -μ 95 88 100 90 atrazine 62.5 Table 13: Compound Ia.29, imazapyr and imazethapyr 1 and __grass atrazine (post-emergence treatment; greenhouse) application rate vermicelli ratio E (g / ha activity Points) Damaged [%] Ia.29 + 3.91 imazapyr + imazethapyr + 3.91 70-atrazine 62.5 40-Ia.29 + 3.91 imazapyr + + 3.91 100 82 imazethapyr 4- atrazine 62.5 86907 -55- 200410634 Table 14: Compound Ia.29, imazapic and imazapyr 2 and grass _Pesticide removal by atrazine (post-germination treatment; greenhouse) Application rate (g / ha active ingredient) Gardenia Kobe commercial hemp Kobe damaged [%] value E Damage [%] value E Ia.29 + 7.81 imazapic + 80-85-imazapyr 7.81 atrazine 125 30-30 Ia.29 + 7.81 imazapic + + 7.81 100 86 100 90 isoam Grass (imazapyr) 4- 1 grass atrazine 1 125 Table 15: Compound Ia.29, imazapic and imazapyr 2 and atrazine's purgative effect (germination Post-treatment; greenhouse) Application rate Hog ratio E (g / ha active ingredient) Impaired [%] Ia.29 + 7.81 azapic) + 80-imazapyr 7.81 atrazine 125 60 Ia.29 + 7.81 1 imazapic + + 7.81 98 92 imazapyr + + atrazine) 125 86907 -56- 200410634 Table 16: Pyrene compound Ia.29, imazapic and imazapyr2 and atrazine's purgative effect (post-germination treatment; Greenhouse) Application rate (g / ha active ingredient) Alexandrium grass ratio E Biako ratio E damage [%] damage [%] Ia.29 + imazapic + imazapyr 3.91 + 3.91 85-80-atrazine 62.5 20-20 Ia.29 + imazapic + imazapyr + atrazine 3.91 + 3.91 + 62.5 100 88 98 84 Table 17 Compound Ia.29, Imazapic and imazapyr 2 and atrazine (post-emergence treatment; greenhouse) Application rate Vermicelli ratio E (g / ha Active ingredient) Impaired [%] Ia.29 + imazapic 4- 3.91 + 70 face imazapyr 3.91 grass removal (atr azine) 62.5 40-Ia.29 + 3.91 1 imazapic + imazapyr _L + 3.91 + 100 82 atrazine 1 62.5 86907 -57- 200410634 1 imazapyr ): Imazethapyr = 1: 3 2 imazapic: imazapyr = 3: 1 86907 58-
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